- Design, synthesis and biological evaluation of novel coumarin-based hydroxamate derivatives as histone deacetylase (HDAC) inhibitors with antitumor activities
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A series of novel coumarin-based hydroxamate derivatives were designed and synthesized as histone deacetylase inhibitors (HDACis). Selective compounds showed a potent HDAC inhibition with nM IC50 values, with the best compound (10e) being nearly 90 times more active than vorinostat (SAHA) against HDAC1. Compounds 10e and 11d also increased the levels of acetylated histone H3 and H4, which is consistent with their strong HDAC inhibition. In addition, 10e and 11d displayed a higher potency toward human A549 and Hela cancer cell lines compared with SAHA. Moreover, 10e and 11d significantly arrested A549 cells at the G2/M phase and enhanced apoptosis. Molecular docking studies revealed the possible mode of interaction of compounds 10e and 12a with HDAC1. Our findings suggest that these novel coumarin-based HDAC inhibitors provide a promising scaffold for the development of new potential cancer chemotherapies.
- Yang, Feifei,Zhao, Na,Song, Jiali,Zhu, Kongkai,Jiang, Cheng-shi,Shan, Peipei,Zhang, Hua
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- Coumarin derivatives as potential inhibitors of acetylcholinesterase: Synthesis, molecular docking and biological studies
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A series of novel hybrids has been synthesized by linking coumarin moiety through an appropriate spacer to various substituted heterocyclic amines and evaluated as dual binding site acetylcholinesterase inhibitors for the treatment of cognitive dysfunction caused by increased hydrolysis of acetylcholine and scopolamine induced oxidative stress. Anti-amnesic activity of the compounds was evaluated using Morris water maze model at a dose of 1?mg/kg with reference to the standard, donepezil. Biochemical estimation of oxidative stress markers (lipid peroxidation, superoxide dismutase, and plasma nitrite) was carried out to assess the antioxidant potential of the synthesized molecules. Among all the synthesized compounds (15a–i, 16a–d, 17a–b), compound 15a [4-[3-(4-phenylpiperazin-1-yl)propoxy]-2H-chromen-2-one] displayed significant antiamnesic activity, AChE inhibitory activity (IC50?=?2.42?μM) and antioxidant activity in comparison to donepezil (IC50?=?1.82?μM). Molecular docking study of 15a indicated that it interacts with all the crucial amino acids present at the CAS, mid-gorge and PAS of TcAChE resulting in increased inhibition of AChE enzyme.
- Singla, Shaffali,Piplani, Poonam
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- Cu (I) Catalyzed One Pot SN-Click Reactions of Halogenated Coumarins and 1-aza-coumarins
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A one pot three component, copper catalyzed azide-alkyne cycloaddition reaction has been employed for the synthesis of bis-coumarinyl triazoles (A–D) using 4-chloro, 4-bromomethyl, 3-bromoacetyl and 4-bromomethyl-1-aza-coumarins (I–IV), sodium azide, and coumarin propargyl ethers (V–IX) in moderate yields.
- Revankar, Hrishikesh M.,Kulkarni, Manohar V.
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- A convenient one-pot synthesis of 4-hydroxycoumarin, 4-hydroxythiocoumarin, and 4-hydroxyquinolin-2(1H)-one
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An improved one-pot synthesis of 4-hydroxycoumarin, 4-hydroxythiocoumarin, and 4-hydroxyquinolin-2(1H)-one from 2-hydroxyacetophenone, 2-mercaptoacetophenone, and 2-aminoacetophenone, respectively, is described. The synthetic strategies involve the acylation and internal ring cyclization. This method is readily amenable to large-scale synthesis of 4-hydroxycoumarin, 4-hydroxythiocoumarin, and 4-hydroxyquinolin-2(1H)-one derivatives in high yields.
- Jung,Jung,Park
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- Synthesis of substituted 4-(4-((3-Nitro-2-oxo-2H-chromene-4-yl)amino)phenyl)morpholine-3-one coumarin derivatives
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A series of novel 4-(4-amino phenyl) morpholine-3-one substituted coumarin derivatives have been prepared by chloramine coupling reaction and were identified. The novel synthetic route involves nucleophilic substitution reaction of 4-chloro-3-nitro-2H-chromene-2- one with 4-(4-amino phenyl)morpholine-3-one. Due to the presence of nitro group in coumarin derivatives make substitution reaction easy and convenient at low temperature. Using DMF as solvent and K2CO3 as base various substituted 4-(4-((3-nitro-2-oxo-2H-chromen- 4-yl)amino)phenyl)morpholine-3-one derivatives (YS-1 to YS-10) can be obtain in good yield and high purity. Structural characterization of all synthesized compound was done by NMR, Mass and IR spectra.
- Sanghani, Yogesh J.,Koradiya, Suresh B.,Patel, Anilkumar S.
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- Synthesis and photooxygenation of furo[3,2-c]coumarin derivatives as antibacterial and DNA intercalating agent
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Syntheses of 2,3-dimethyl-4H-furo[3,2-c]coumarin and 3-phenyl-4H-furo[3,2- c]coumarin as angular furocoumarins were carried out through Williamson reaction of 4-hydroxycoumarin with α-haloketones followed by cyclization. Photooxygenation of the synthesized furocoumarin derivatives was performed and the photoproducts were isolated and characterized. The affinity of 2,3-dimethyl-4H-furo[3,2-c]coumarin towards DNA and the antibacterial activity were evaluated and compared with 8-methoxypsoralen (8-MOP). Syntheses of 2,3-dimethyl-4H-furo[3,2-c]coumarin and 3-phenyl-4H-furo[3,2-c]coumarin as angular furocoumarins were carried out through Williamson reaction of 4-hydroxycoumarin with α-haloketones followed by cyclization. Photooxygenation of the synthesized furocoumarin derivatives was performed and the photoproducts were isolated and characterized. The affinity of 2,3-dimethyl-4H-furo[3,2-c]coumarin towards DNA and the antibacterial activity were evaluated and compared with 8-methoxypsoralen (8-MOP). Copyright
- Al-Sehemi, Abdullah G.,El-Gogary, Sameh R.
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- Synthesis and biological evaluation of 4 arylcoumarin analogues as tubulin-targeting antitumor agents
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The synthesis of twenty-six 4-arylcoumarin analogues of combretastatin A-4 (CA-4) led to the identification of two new compounds (25 and 26) with strong cytotoxic activity. Both compounds had a high cytotoxic effect on a CA-4-resistant colon adenocarcinoma cell line (HT29D4). The compounds affected cell cycle progression characterized by a mitotic block. The activity of these compounds against microtubules both in vitro and in cells was examined and both compounds were found to potently inhibit in vitro microtubule formation via a sub-stoichiometric mode like CA-4. By immunofluorescence, it was observed that both compounds induced strong microtubule network disruption. Our results provide a strong experimental basis to develop new potent anti-tubulin molecules targeting CA-4-resistant cancer cells.
- Mutai, Peggoty,Breuzard, Gilles,Pagano, Alessandra,Allegro, Diane,Peyrot, Vincent,Chibale, Kelly
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- Chromenone derivatives as a versatile scaffold with dual mode of inhibition of HIV-1 reverse transcriptase-associated Ribonuclease H function and integrase activity
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A number of compounds targeting different processes of the Human Immunodeficiency Virus type 1 (HIV-1) life cycle have been developed in the continuing fight against AIDS. Coumarin-based molecules already proved to act as HIV-1 Protease (PR) or Integrase (IN) inhibitors and also to target HIV-1 reverse transcriptase (RT), blocking the DNA-dependent DNA-polymerase activity or the RNA-dependent DNA-polymerase activity working as common NNRTIs. In the present study, with the aim to exploit a coumarin-based scaffold to achieve the inhibition of multiple viral coded enzymatic functions, novel 4-hydroxy-2H, 5H-pyrano (3, 2-c) chromene–2, 5–dione derivatives were synthesized. The modeling studies calculated the theoretical binding affinity of the synthesized compounds on both HIV-1 IN and RT-associated Ribonuclease H (RNase H) active sites, which was confirmed by biological assays. Our results provide a basis for the identification of dual HIV-1 IN and RT RNase H inhibitors compounds.
- Esposito, Francesca,Ambrosio, Francesca Alessandra,Maleddu, Rita,Costa, Giosuè,Rocca, Roberta,Maccioni, Elias,Catalano, Raffaella,Romeo, Isabella,Eleftheriou, Phaedra,Karia, Denish C.,Tsirides, Petros,Godvani, Nilesh,Pandya, Hetal,Corona, Angela,Alcaro, Stefano,Artese, Anna,Geronikaki, Athina,Tramontano, Enzo
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- Microwave-assisted synthesis and antifungal activity of novel fused Osthole derivatives
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Based on the microwave-assisted synthetic protocol developed in our previous work, we have synthesized a series of novel furo[3,2-c]coumarins as fused Osthole derivatives, via the reaction of 4-hydroxycoumarins and β-ketoesters catalyzed by DMAP. All the target compounds were evaluated in?vitro for their antifungal activity against six phytopathogenic fungi, some compounds exhibited potential activity in the primary assays. Especially compounds 6c, 7b, 8b and 8c (shown in Fig.?1) were the most active ones, EC50values of these four compounds against Colletotrichum capsica, Botrytis cinerea and Rhizoctonia solani were further investigated. 6c was identified as the most promising candidate with the EC50value at 0.110?μM against Botrytis cinerea and 0.040?μM against Colletotrichum capsica, respectively, representing better antifungal activity than that of the commonly used fungicide Azoxystrobin.
- Zhang, Ming-Zhi,Zhang, Rong-Rong,Wang, Jia-Qun,Yu, Xiang,Zhang, Ya-Ling,Wang, Qing-Qing,Zhang, Wei-Hua
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- One-pot two-step synthesis of 3-iodo-4-aryloxy coumarins and their Pd/C-catalyzed annulation to coumestans
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An efficient protocol for the synthesis of various coumestans from the intramolecular annulation of 3-iodo-4-aryloxy coumarins through C-H activation has been developed. When 3-iodo-4-aryloxy coumarins were treated with 10% Pd/C (0.3 mol% Pd) in the presence of sodium acetate, the corresponding coumestans were produced in good to excellent yield. Reusability of the palladium catalyst was investigated in up to three consecutive cycles and it was found that the yield of the reaction was almost unaltered. Sequential iodination and O-arylation of 4-hydroxy coumarins leading to the 3-iodo-4-aryloxy coumarins were also achieved in a one-pot two-step process starting from aryl iodides in high yield. Pivalic acid was revealed to be the most effective additive for the later method to produce 3-iodo-4-phenoxy coumarins. Different functional groups bearing electron-donating as well as withdrawing groups are also tolerant to the reaction conditions.
- Panda, Niranjan,Mattan, Irshad
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- Expeditious synthesis, antileishmanial and antioxidant activities of novel 3-substituted-4-hydroxycoumarin derivatives
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A series of novel 3-substituted-4-hydroxycoumarin derivatives 6(a–l) were synthesized in high yield using one-pot three component coupling reaction catalyzed by ceric ammonium nitrate. These compounds were evaluated for antileishmanial activity against Leishmania donovani promastigotes and antioxidant activity (DPPH-radical scavenging activity). Two compounds, 6h (IC50 = 9.90 μmol/L) and 6i (IC50 = 6.90 μmol/L) displayed potent antileishmanial activity when compared with standard antileishmanial agents pentamidine (IC50 = 16.15 μmol/L) and miltefosine (IC50 = 12.50 μmol/L). Three compounds, 6c (IC50 = 10.79 μmol/L), 6h (IC50 = 10.60 μmol/L), and 6i (IC50 = 10.73 μmol/L) showed significant antioxidant activity favorably with the antioxidant standards butylated hydroxy toluene (IC50 = 16.47 μmol/L) and ascorbic acid (IC50 = 12.69 μmol/L). A molecular docking study of compounds 6(a–l) suggested a possible mode of binding with the Adenine phosphoribosyltransferase enzyme of L. donovani. ADME properties were predicted in silico and support the potential of 6(a–l) to show favorable drug-like properties.
- Zaheer, Zahid,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Patil, Rajendra H.
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- Synthesis and antiproliferative activity of hybrid thiosemicarbazone derivatives bearing coumarin and d-galactose moieties with EGFR inhibitory activity and molecular docking study
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A series of substituted N-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)thiosemicarbazones 5a–5j of substituted 3-acetylcoumarins were synthesized with yields of 45–68%. All synthesized thiosemicarbazones were evaluated for cytotoxic activity against several cancer cell lines, such as human breast adenocarcinoma cells MCF7, human liver cancer cells HepG2, human cervical cancer cells HeLa, human melanoma cancer cells SK-Mel-2, and human lung cancer cells LU-1 by using the standard MTT assay. The IC50 values for these cancer cell lines were 1.28–11.81 μM (for MCF-7), 1.53–22.12 μM (for HepG2), 1.43–48.16 μM (for HeLa), 1.82–14.62 μM (for SK-Mel-2), and 1.74–14.62 μM (for LU-1). Most of the compounds were noncytotoxic against human WI-38 normal cell line (IC50 > 16.9 μM). The antiproliferative mechanisms were studied via EGFR inhibition and molecular docking. Docking studies revealed that there are strong interactions between a typical compound with the receptor of the EGFR tyrosine kinase domain with Erlotinib. [Figure not available: see fulltext.]
- Toan, Vu Ngoc,Thanh, Nguyen Dinh
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- Combined Claisen Rearrangement and Oxidative Cyclization as a Route to Hydroxymethyl Dihydrofuran-Annulated Coumarins
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A convenient and simple method for the synthesis of novel 3,4-dihydrofuran-annulated coumarins, 3-(hydroxymethyl)-2H-furo[3,2-c]chromen-4(3H)-ones 5a, 5b, 5c, 5d, 5e, 5f, 5g, by combined Claisen rearrangement and intramolecular regioselective oxidative cyclization of 4-O-allyl coumarin intermediates 3a, 3b, 3c, 3d, 3e, 3f, 3g using inexpensive oxidizing agent m-CPBA is described. The reaction proceeds smoothly by tandem epoxidation/regioselective 5-exo-tet-intramolecular ring opening. The structures of synthesized compounds are established on the basis of spectral data including IR, 1H NMR, and mass and elemental analyses.
- Jayaprakash, Rao Y.,Chakravarthula, Venu
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- Synthesis and biological evaluation of bis-N2,N2′-(4-hydroxycoumarin-3-yl)ethylidene]-2,3-dihydroxysuccinodihydrazides
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A series of N2,N2′-bis[4-hydroxycoumarin-3-yl)ethylidene]-2,3-dihydroxysuccino-hydrazides, containing 4-hydroxycoumarin, hydrazine and tartaric acid moieties, have been prepared and examined for possible biological activity. Several of these compounds exhibit promising HIV-1 integrase inhibition (IC50 = 3.5 μM), and anti-T. brucei (32% viability) and anti-mycobacterial (Visual MIC90 = 15.63 μM) activity.
- Hoppe, Heinrich C.,Isaacs, Michelle,Kaye, Perry T.,Krause, Rui W. M.,Manyeruke, Meloddy H.,Seldon, Ronnett,Tshiwawa, Thendamudzimu,Warner, Digby F.
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- Combining silver catalysis and organocatalysis: A sequential michael addition/hydroalkoxylation one-pot approach to annulated coumarins
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A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed. By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good to excellent enantioselectivities (up to 99% ee) via a Michael addition/hydroalkoxylation reaction. Depending on the substituents on the enynone, the synthesis of annulated six-membered rings is also feasible.
- Hack, Daniel,Chauhan, Pankaj,Deckers, Kristina,Hermann, Gary N.,Mertens, Lucas,Raabe, Gerhard,Enders, Dieter
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- SELENIUM ASSISTED CARBONYLATION OF ALKYL ARYL KETONES WITH CARBON MONOXIDE
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Selenium assisted carbonylation of alkyl aryl ketones with carbon monoxide leading to formation of 1,3-dicarbonyl compounds as C-carbonylated products is described. o-Hydroxyacetophenone (7a) and its derivatives (7b, 7c and 7d) have been converted to the corresponding 4-hydroxycoumarins (8a, 8b, 8c and 8d) in moderate to quantitative yields by treatment with an equivalent of selenium and carbon monoxide with concomitant formation of hydrogen selenide (9) (Eq.(8)).It was further revealed that oxidation of in situ formed hydrogen selenide to selenium with an appropriate oxidizing agent such as nitrobenzene permitted catalytic use of selenium for the carbonylation of 7.Possible rationalizations for the formation of 4-hydroxycoumarins are suggested.
- Ogawa, Akiya,Kambe, Nobuaki,Murai, Shinji,Sonoda, Noboru
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- Facile Synthesis of 4-Hydroxycoumarins by Sulfur-Assisted Carbonylation of 2'-Hydroxyacetophenones with Carbon Monoxide
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4-Hydroxycoumarins (4-hydroxy-2-oxo-2H-1-benzopyrans) were synthesized in good to excellent yields by C-carbonylation of 2'-hydroxyacetophenones with carbon monoxide in the presence of sulfur and bases.This is the first example of sulfur-assisted C-carbonylation with carbon monoxide.
- Mizuno, Takumi,Nishiguchi, Ikuzo,Hirashima, Tsuneaki,Ogawa, Akiya,Kambe, Nobuaki,Sonoda, Noboru
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- Synthesis of furo[3,2-c]coumarins via I2/TBHP-mediated reaction of 4-hydroxycoumarins with terminal alkynes
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An efficient I2/TBHP-mediated process for the formation of furo[3,2-c]coumarins from readily available materials has been developed. This process for the formation of furo[3,2-c]coumarins is quite environmental friendly and atom-economical.
- Chu, Xianglong,Tang, Ziqiang,Ma, Jiangshan,He, Libowen,Feng, Lei,Ma, Chen
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- Synthesis and reactivity of boron difluoride complexes of N,N-dimethylsalicylacetamide
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The synthesis and reactivity of a series of BF2 complexes of N,N-dimethylsalicylacetamide was examined.
- Morris,Fang,Wishka,Han
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- Selenium-assisted Carbonylation of o-Hydroxyacetophenone with Carbon Monoxide
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Selenium-assisted carbonylation of o-hydroxyacetophenone (1) with carbon monoxide in the presence of a strongly basic tertiary amine gave 4-hydroxycoumarin (2) as a C-carbonylated product in a high yield.
- Ogawa, Akiya,Kondo, Kiyoshi,Murai, Shinji,Sonoda, Noboru
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- Sulfonamides containing coumarin moieties selectively and potently inhibit carbonic anhydrases II and IX: Design, synthesis, inhibitory activity and 3D-QSAR analysis
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A series of sulfonamides containing coumarin moieties had been prepared that showed a very interesting profile for the inhibition of two human carbonic anhydrase inhibitors. These compounds were evaluated for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA II and the tumor-associated isozyme hCA IX. The most potent inhibitor against hCA II and IX were compounds 5d (IC50 = 23 nM) and 5l (IC50 = 24 nM), respectively. These sulfonamides containing coumarin moieties may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly. Eighteen compounds were scrutinized by CoMFA and CoMSIA techniques of 3D quantitative structure-activity relationship. Nine of the compounds were evaluated for cytotoxicity against human macrophage.
- Wang, Zhong-Chang,Qin, Ya-Juan,Wang, Peng-Fei,Yang, Yong-An,Wen, Qing,Zhang, Xin,Qiu, Han-Yue,Duan, Yong-Tao,Wang, Yan-Ting,Sang, Ya-Li,Zhu, Hai-Liang
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- Design, Synthesis, and Evaluation of in Vitro and in Vivo Anticancer Activity of 4-Substituted Coumarins: A Novel Class of Potent Tubulin Polymerization Inhibitors
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In this paper, a series of novel 4-substituted coumarin derivatives were synthesized. Among these compounds 34, 39, 40, 43, 62, 65, and 67 exhibited significant antiproliferative activity toward a panel of tumor cell lines at subnanomolar IC50 values. Compound 65 showed potent antiproliferative ability (IC50 values of 7-47 nM) and retained full activity in multidrug resistant cancer cells. Compound 65 caused G2/M phase arrest and interacted with the colchicine-binding site in tubulin, as confirmed by immune-fluorescence staining, microtubule dynamics assays, and competition assays with N,N′-ethylene-bis(iodoacetamide). Compound 65 reduced the cell migration and disrupted capillary-like tube formation in HUVEC cells. Importantly, compound 65 significantly and dose-dependently reduced tumor growth in four xenografts models including paclitaxel sensitive and resistant ovarian tumors (A2780s and A2780/T), adrmicycin sensitive and resistant breast tumors (MCF-7 and MCF-7/ADR), suggesting that compound 65 is a promising novel antimitotic compound for the potential treatment of cancer.
- Cao, Dong,Liu, Yibin,Yan, Wei,Wang, Chunyu,Bai, Peng,Wang, Taijin,Tang, Minghai,Wang, Xiaoyan,Yang, Zhuang,Ma, Buyun,Ma, Liang,Lei, Lei,Wang, Fang,Xu, Bixue,Zhou, Yuanyuan,Yang, Tao,Chen, Lijuan
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- Novel conjugates of podophyllotoxin and coumarin: Synthesis, cytotoxicities, cell cycle arrest, binding CT DNA and inhibition of Topo IIβ
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A series of conjugates of podophyllotoxin and coumarin were prepared using the click reaction, and their cytotoxicities against A549, HepG2, HeLa, and LoVo cells were evaluated. Among them, compound 14e exhibited the strongest cytotoxicities against these cancer cells with IC50 values of 4.9–17.5 μM. Furthermore, 14e disrupted microtubules and induced cell cycle arrest at G1 phase by regulating P21 and Cyclin D1 in LoVo cells. In addition, 14e bond CT DNA and selectively inhibited Topo IIβ over Topo IIα. Molecular docking model showed that 14e appeared to form stable hydrogen bonds with several DNA bases and residue Gln778. Taken together, these conjugates have the potential to be developed as anti-tumor drugs.
- Hao, Shu-Yi,Feng, Shi-Liang,Wang, Xing-Rong,Wang, Zhichao,Chen, Shi-Wu,Hui, Ling
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- Photooxygenation of chromone-2-carboxylic acid: Identification of ketohydroperoxide using a chemiluminescence technique
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Irradiation of chromone-2-carboxylic acid in aerated ethanol solution gives 4-hydroxycoumarine with the quantum yield of 0.02. The reaction proceeds via the decarboxylation followed by the addition of the oxygen molecule. Chemiluminescence measuring was successfully applied to detect the ketohydroperoxide intermediate in the photoreaction.
- Kawata, Hiroki,Kumagai, Tsutomu,Niizuma, Shigeya
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- Energy transfer in coumarin-sensitised lanthanide luminescence: Investigation of the nature of the sensitiser and its distance to the lanthanide ion
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A series of lanthanide complexes [Ln(dpxCy)3]3- have been synthesised. The ligands are composed of a coordinating dipicolinic acid backbone decorated with a polyoxyethylene arm fitted with a coumarin moiety at its extremity. The nature of the coumarin as well as the length of the linker have been varied. Upon excitation at 320 nm, the coumarin exclusively acts as an antenna while the dipicolinic acid core is not excited. Upon excitation below 300 nm, both parts are excited. With europium as a metal centre, the relaxation of the europium ion (intrinsic quantum yield ΦEuEu and radiative lifetime τr) is constant for all the studied ligands. Therefore, the observed differences in overall quantum yield (ΦEuL) in such systems come exclusively from the variation of the terminal coumarin. The overall quantum yields of the studied complexes are low (ΦEuL sens), the distance between the coumarin sensitiser and the lanthanide centre was explored in solution and compared to the solid state. In the solid state, a dramatic effect was confirmed, with an improvement of 80% in the quantum yield ΦEuL for short linkers ((-CH2CH2O-)n with n = 1 compared to n = 3). By monitoring the lifetime decay of the excited state of the lanthanide cation with nanosecond vs. microsecond time-resolved spectroscopy at low temperature, the sensitisation of the lanthanide ions by coumarin derivatives was demonstrated to mainly occur through the singlet excited state of the coumarin and not via the usual triplet pathway. No evidence of a different behaviour at room temperature was found by transient triplet-triplet absorption spectroscopy.
- Andres, Julien,Chauvin, Anne-Sophie
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- Design, synthesis, and mechanism of dihydroartemisinin-coumarin hybrids as potential anti-neuroinflammatory agents
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Cancer patients frequently suffer from cancer-related fatigue (CRF), which is a complex syndrome associated with weakness and depressed mood. Neuroinflammation is one of the major inducers of CRF. The aim of this study is to find a potential agent not only on the treatment of cancer, but also for reducing CRF level of cancer patients. In this study, total-thirty new Dihydroartemisinin-Coumarin hybrids (DCH) were designed and synthesized. The in vitro cytotoxicity against cancer cell lines (HT-29, MDA-MB-231, HCT-116, and A549) was evaluated. Simultaneously, we also tested the anti-neuroinflammatory activity of DCH. DCH could inhibit the activated microglia N9 release of NO, TNF-α, and IL-6. The docking analysis was shown that MD-2, the coreceptor of TLR4, might be one of the targets of DCH.
- Yu, Haonan,Hou, Zhuang,Yang, Xiaoguang,Mou, Yanhua,Guo, Chun
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- Copper(II)-Catalyzed Tandem Reaction: Synthesis of Furo[3,2- c]coumarin Derivatives and Evaluation for Photophysical Properties
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An efficient protocol for synthesizing furo[3,2-c]coumarin derivatives is described. The novel reaction could afford the desired furocoumarins with good to excellent yields in a mild and rapid manner. Large substrate scope screening and scale-up preparation have also been accomplished, and selected compounds were evaluated for their photophysical properties.
- Feng, Xi,Qin, Zhen,Cheng, Xinying,Liu, Dongyu,Peng, Yinghe,Huang, Huidan,Song, Bin,Bian, Jinlei,Li, Zhiyu
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supporting information
p. 12537 - 12548
(2021/09/20)
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- TRICYCLIC COMPOUNDS ACTING ON CRBN PROTEINS
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The present invention discloses a series of tricyclic compounds and use thereof in preparing a medicament for treating a disease related to CRBN protein. Specifically, the present invention discloses a derivative compound of formula (1) or a pharmaceutically acceptable salt thereof.
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Paragraph 0155-0156
(2021/07/17)
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- Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes
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An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.
- Ding, Guangni,Fan, Sijie,Wang, Jingyang,Wang, Yu,Wu, Xiaoyu,Xie, Xiaomin,Yang, Liqun,Zhang, Zhaoguo
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supporting information
(2021/09/28)
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- Novel coupled molecules from active structural motifs of synthetic and natural origin as immunosuppressants
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Introduction: Nitric oxide (NO) is an important mediator in the pathogenesis and control of immune system-related disorders and its levels are modulated by inducible NO synthase (iNOS). Oxidative stress is another pathological indication in majority of autoimmune disorders. The present study aims at the development of coupled molecules via selection of pharmacophores for both immunomodulatory and antioxidant activities through iNOS inhibition. Methods: Variedly substituted coumarin moieties are coupled with naturally occurring phenols through an amide linkage and were predicted for activities using computer-based program PASS. The compounds predicted to have dual activities were synthesized. Docking studies were carried out against iNOS (PDB 1R35) and compounds having good docking score were evaluated for immunomodulatory and antioxidant activities. Results: The synthesized compounds were found to be pure and were obtained in good yields. Compounds with maximum docking score (YR1a, YR2e, YR2c and YR4e) were selected for evaluation by in vitro models. Compounds YR2e and YR2c markedly inhibited the reduction of NBT dye and showed maximum percent iNOS inhibition. In DPPH assay, compound YR4e was observed as the most potent antioxidant (EC50 0.33 μM/mL). Based on these studies, compounds YR2e and YR2c were selected for haemagglutination test. Compound YR2e was observed as the most active immunosuppressant with maximal inhibitory ability of iNOS and NBT reduction and lower HAT value of 3.5. Conclusion: Compound YR2e can be utilized as a pharmacological agent in the prevention or treatment of immunomodulatory diseases such as tumors, rheumatoid arthritis, ulcerative colitis, organ transplant and other autoimmune disorders.
- Minhas, Richa,Bansal, Gulshan,Bansal, Yogita
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p. 544 - 554
(2020/06/21)
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- Synthesis and anti-inflammatory activity of 2-oxo-2H-chromenyl and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates
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Cycloaddition reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehydes (3a-g) and 4-chloro-2H-chromene-3-carbaldehydes (7a-h) with activated alkynes (4a-b) provided the 2-oxo-2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (5a-n) and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (8a-p). All the prepared compounds were screened for anti-inflammatory activity. In vitro anti-inflammatory activity data demonstrated that the compounds 5g, 5i, 5k-l and 8f are effective among the tested compounds against TNF-α (1.108 ± 0.002, 0.423 ± 0.022, 0.047 ± 0.001, 0.070 ± 0.002 and 0.142 ± 0.001 μM) in comparison with standard compound Prednisolone (0.033 ± 0.002 μM). Based on in vitro results, three compounds (5i, 5k and 8f) have been selected for in vivo experiments and these compounds are identified as better compounds with respect to anti-inflammatory activity in LPS induced mice model. Compound 5i was identified as potent and showed significant reduction in TNF-α and IL-6.
- Bhimapaka, China Raju,Karri, Shailaja,Kuncha, Madhusudana,Kurma, Siva Hariprasad,Sistla, Ramakrishna
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- Design, synthesis, biological and in silico evaluation of coumarin-hydrazone derivatives as tubulin targeted antiproliferative agents
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Coumarin-based different series of hydrazone derivatives were synthesized and evaluated for anticancer activity against four different human cancer cell lines. The activity of the compounds were compared with doxorubicin as a standard drug and all the compounds exhibited good to moderate cytotoxicity with IC50 values ranging from 6.07 to 60.45 μM against all the examined cancer cell lines. Based on the screening results, it was concluded that the compounds 12a and 18a were the most promising medicinal entities. In vitro tubulin polymerisation inhibition assay was performed for the compounds 12a and 18a and these two compounds displayed good potency when compared with colchicine as the standard drug. The interaction of these compounds with tubulin protein was also studied with the help of molecular docking technique using Discovery studio software. Furthermore, the molecular and ADMET properties of the compounds were computed with Osiris property software and PreADMET server. The compounds exhibited exciting in vitro and in silico results. Hence we propose that the compounds 12a and 18a could be developed as tubulin targeted potential antiproliferative agents.
- Govindaiah,Dumala, Naresh,Mattan, Irshad,Grover, Paramjit,Jaya Prakash
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- Stereoselective synthesis of carbohydrate fused pyrano[3,2-c]pyranones as anticancer agents
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Pyrano[3,2-c]pyranone is an important structural motif present in many natural products exhibiting diverse biological activities. Two series of carbohydrate fused pyrano[3,2-c]pyranone derivatives (n = 20) were efficiently synthesized starting from 2-C-formyl galactal and 2-C-formyl glucal, reacting with various 4-hydroxycoumarins in a very short reaction time (10 min) under microwave assisted conditions. The anticancer activity of these synthesized pyrano[3,2-c]pyranones was determined in detail through cellular assays against MCF-7 (breast), MDA-MB-231 (breast) and HepG2 (liver) cancer cell lines. The newly synthesized pyrano[3,2-c]pyranones were screened for their cell-viability and anti-proliferative activity against MCF-7, MDA-MB-231 and HepG2 cell lines. Compounds 12, 13 and 14 exhibited high growth inhibitory potencies selectively against MCF-7 cells with half-maximal inhibitory concentration (IC50) values of 19.9, 14.5 and 10.9 μM respectively. Compounds 12, 13, 14, 15 and 19 inhibited the growth of MDA-MB-231 cells (breast) by 43, 44, 37, 31 and 45% respectively. However, no inhibitory effect was observed for these compounds in the human liver cancer cell line (HepG2) and normal cell lines (HEK293, human embryonic kidney cells). Mechanistic studies showed that these compounds alter the cell morphology and cause G2/M arrest in MCF-7. Further studies showed that compounds 12, 13 and 14 significantly inhibited cell migration which was accompanied by altered microtubule distribution. An enhanced accumulation of these compounds in cells was observed as compared to the 4-hydroxycoumarins precursor in the intracellular uptake assay. These findings confirm that carbohydrate fused pyrano[3,2-c]pyranones are better candidates for anticancer activity.
- Kumari, Priti,Gupta, Sonal,Narayana, Chintam,Ahmad, Shakeel,Vishnoi, Nidhi,Singh, Shailja,Sagar, Ram
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supporting information
p. 13985 - 13997
(2018/08/21)
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- 1,2-Benzisoxazole-3-acetamide derivatives as dual agents for DPP-IV inhibition and anticancer activity
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Herein, we have designed various benzisoxazole acetamide derivatives with and without glycine spacer as DPP-IV inhibitors. Compounds 9a–d and 11a–e were synthesized and screened for their in vitro DPP-IV inhibition. Compounds 11a and 11c showed moderate activity for DPP-IV inhibition, whereas other remained inactive at 25–200 μM concentrations. DPP-IV inhibition can be a good strategy for modulating diabetes and cancer; hence, we have screened compounds 9a–d and 11a–e for their anticancer activity using MTT assay against A549 and MCF7 cell lines. Compounds 9a–d without glycine spacer have shown good anticancer activity compared to compounds 11a–e with glycine spacer. Compound 9b has shown moderate activity with IC50 values 4.72 ± 0.72 and 4.39 ± 0.809 μM against A549 and MCF7 cell lines, respectively. Interestingly, compound 9c with cyano group has shown very good anticancer activity with IC50 2.36 ± 0.34 μM against MCF7 cell line as compared to fluorouracil with IC50 45.04 ± 1.02 μM.
- Karandikar, Shubhendu,Soni, Rina,Soman, Shubhangi S.,Umar, Shweta,Suresh, Balakrishnan
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supporting information
p. 2877 - 2887
(2018/11/06)
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- Unexpected C-N bond formation via Smiles rearrangement: One pot synthesis of N -arylated coumarin/pyran derivatives
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A conceptually new and one-pot method for the synthesis of N-arylated coumarin/pyran derivatives via Smiles rearrangement. The reaction of 4-bromocoumarin/pyran with 2-amino phenols affords O-arylated coumarin/pyran which subsequently rearranges into N-arylated coumarin/pyran under mild reaction conditions in good yields.
- Kumar, K. Shiva,Ramulu, Meesa Siddi,Kumar, N. Praveen
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supporting information
p. 11276 - 11279
(2018/07/25)
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- Hydroxamic acids compound containing coumarin structure, application and preparation method of hydroxamic acids compound
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The invention provides hydroxamic acids HDACi which is novel in structure and contains a coumarin structure. The hydroxamic acids HDACi comprise pharmaceutically acceptable salts, metabolite, isomer,prodrug and the like. Meanwhile, the invention also discloses a preparation method of the compound. On the basis of a coumarin key structure module, a hydroxamic acid structural framework is introduced, a novel hydroxamic acids micromolecular organic compound which contains a coumarin structure is designed and synthesized, the compound has the advantages of coumarin and the advantages of hydroxamic acid, and the obtained compound which serves as a histone deacetylase inhibitor can be placed in drugs for preventing and treating cancers or inflammations; and the compound can further be used forinducing drugs for treating tumors after chemotherapy fails due to acquired drug resistance.
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Paragraph 0022
(2018/11/03)
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- Difluoromethylthiolation of Phenols and Related Compounds with a HF2CSO2Na/Ph2PCl/Me3SiCl System
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A novel HF2CSO2Na/Ph2PCl/Me3SiCl system is disclosed for the late-stage direct difluoromethylthiolation of Csp2 and Csp3 nucleophiles. Difluoromethylthiolation of phenols and naphthols proceeded nicely under this system to regioselectively provide corresponding SCF2H compounds in good yields. Other substrates such as indoles, pyrroles, pyrazoles, enamines, ketones, and β-keto esters were also transformed to corresponding SCF2H products in good yields. The late-stage direct difluoromethylthiolation of a number of natural products and pharmaceutically attractive molecules was also achieved.
- Huang, Zhongyan,Matsubara, Okiya,Jia, Shichong,Tokunaga, Etsuko,Shibata, Norio
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supporting information
p. 934 - 937
(2017/02/26)
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- Affinity-based small fluorescent probe for NAD(P)H:quinone oxidoreductase 1 (NQO1). Design, synthesis and pharmacological evaluation
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NQO1 is a dimeric flavoprotein which intimately associated with cancer and overexpressed in the cytosol of numerous human tumor cells. Given that the cellular environment is quite dynamic and versatile, further investigation of the function of NQO1 depends on tools for specific detection of it. Currently, several activity-based assays have been developed to detect NQO1-expressing cancerous tissues. Herein, we report the development of a functional affinity-based small-molecule probe which is composed of a potent small-molecule NQO1 inhibitor 3d as the recognition group, a linker and the fluorophores group FITC. The probe exhibits good inhibitory activity of NQO1 and has been successfully used to label the protein in A549 cells at the micromolar level. These features make the probe favorable for mechanistic studies and cancer diagnostic biomarker. Based on these preliminary results, our laboratory will focus on the further development of fluorescent probe for NQO1, which could be anticipated to be applied in physiological and pathological studies of NQO1.
- Bian, Jinlei,Li, Xiang,Xu, Lili,Wang, Nan,Qian, Xue,You, Qidong,Zhang, Xiaojin
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p. 828 - 839
(2017/02/10)
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- Reaction of 4-hydroxycoumarin or its O-substituted derivatives with diatomic interhalogens: ICl and IBr
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Herein, we present some aspects regarding the iodination/bromination of 4-hydroxycoumarin or its O-methyl or O-acetyl derivatives with iodine monochloride or iodine monobromide as halogenation reagents. Also, the investigation of photochemical transformation of the three 3-iodocoumarins was investigated for the first time.
- Popa, Marcel Mirel,Draghici, Constantin,Barbu, Loredana,Dumitrescu, Denisa E.,Dumitrascu, Florea
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supporting information
p. 344 - 350
(2017/02/10)
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- Synthesis, Cytotoxic Evaluation, and In Silico Studies of 4-Substituted Coumarins
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Two series of coumarins possessing the aniline- and heterocyclic ring at 4thposition have been synthesized and evaluated for their in vitro cytotoxic activity against MCF-7 cancer cell line in MTT assay. Structure activity relationship (SAR) studies reveal that the electron donor group at position-8 of coumarin played an important role in cytotoxic activity. Compound VIId showed the potent cytotoxic activity followed by compound Xa with IC50= 6.25 and 6.50 μM, respectively. A docking study has also been carried out for the most potent compound to get an insight into molecular interactions with p50 subunit of NF-κB protein.
- Kaur, Prabhjot,Gill, Rupinder Kaur,Singh, Gagandip,Bariwal, Jitender
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p. 1519 - 1527
(2016/09/23)
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- Synthesis and biological evaluation of novel phosphoramidate derivatives of coumarin as chitin synthase inhibitors and antifungal agents
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A series of novel phosphoramidate derivatives of coumarin have been designed and synthesized as chitin synthase (CHS) inhibitors. All the synthesized compounds have been screened for their chitin synthase inhibition activity and antimicrobial activity in vitro. The bioactive assay manifested that most of the target compounds exhibited good efficacy against CHS and a variety of clinically important fungal pathogens. In particular, compound 7t with IC50 of 0.08 mM against CHS displayed stronger efficiency than the reference Polyoxin B with IC50 of 0.16 mM. In addition, the apparent Ki values of compound 7t was 0.096 mM while the Km of Chitin synthase prepared from Candida tropicalis was 3.86 mM for UDP-Nacetylglucosamine, and the result of the Ki showed that the compounds was a non-competitive inhibitor of the CHS. As far as the antifungal activity is concerned, compounds 7o, 7r and 7t were highly active against Aspergillus flavus with MIC values in the range of 1 μg/mL to 2 μg/Ml while the results of antibacterial screening showed that these compounds have negligible actions to the tested bacteria. These results indicated that the design of these compounds as antifungal agents was rational.
- Ji, Qinggang,Ge, Zhiqiang,Ge, Zhixing,Chen, Kaizhi,Wu, Hualong,Liu, Xiaofei,Huang, Yanrong,Yuan, Lvjiang,Yang, Xiaolan,Liao, Fei
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p. 166 - 176
(2015/12/04)
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- Microwave-assisted synthesis and antifungal activity of novel coumarin derivatives: Pyrano[3,2-c]chromene-2,5-diones
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A series of novel fused coumarin analogues pyrano[3,2-c]chromene-2,5-diones have been synthesized through an optimized microwave-assisted protocol. All target compounds were tested and evaluated for their antifungal activity against Botrytis cinerea, Colletotrichum copsica, Alternaria solani, Gibberella zeae and Rhizoctorzia solani. The bioassay results indicated that some of the compounds exhibited potent antifungal activities at concentration less than 50 ppm. For the compounds 5d, 6c and 7b, EC50 values against B. cinerea were as low as 0.141, 0.082 and 0.091 μM, respectively, which represents better antifungal activity than that of the commonly used fungicide Azoxystrobin. Compounds 5d (57%) and 6c (55%) also exhibited more effective control than Azoxystrobin (44%) against Colletotrichum capsica.
- Zhang, Rong-Rong,Liu, Jia,Zhang, Yu,Hou, Meng-Qing,Zhang, Ming-Zhi,Zhou, Fenger,Zhang, Wei-Hua
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- Study of solvatochromic behavior and antimicrobial activities of some newly synthesized bis-azo-dapsone congeners
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In the present study, a series of new bisazo dyes derived from dapsone have been synthesized in one step, using diazotized coupling reaction and evaluated for their in-vitro antimicrobial activity. Ampicillin and fluconazole have been taken as reference antibiotics (RA). The structure of synthesized compounds are confirmed by different spectral techniques viz. elemental analysis, 1H NMR, UV-Vis, FT-IR and mass spectrometry. The solvatochromic behavior of the synthesized compounds are also studied by UV-Vis spectrometry. The compound 4b has been observed with significant antibacterial activity against Shigella flexneri, Escherichia coli, Vibrio cholera and Streptococcus mitis in comparison to standard drug whereas all the compounds except 4f show significant antifungal activity against Aspergillus niger. The results have been statistically interpreted by one way analysis-of variance (ANOVA) followed by Dunnett's Post Hoc test. Exploitation of dapsone molecule by the attachment of different nucleophiles may be responsible for the significant increase of antimicrobial activity. However, the 8-hydroxy quinoline linked bisazo dapsone showed highest significant antimicrobial activity than the other newly synthesized bisazo dapsone analogues in comparison to RA.
- Sahoo, Jyotirmaya,Kumar, Paidesetty Sudhir
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p. 724 - 733
(2017/01/18)
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- A New Protocol for Total Synthesis of Natural Product Frutinone A and Its Derivatives
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A new protocol for total synthesis of natural product frutinone A was accomplished in three steps by using inexpensive 2′-hydroxyacetophenone as starting material. The key intermediate 3-(2-chlorobenzoyl)-4-hydroxycoumarin was synthesized in one pot through Baker-Venkataraman rearrangement of 2-acetylphenyl 2-chlorobenzoate followed by introduction of methyl chloroformate under basic conditions. Then, base-promoted intramolecular nucleophilic substitution reaction of 3-(2-chlorobenzoyl)-4-hydroxycoumarin provided frutinone A in excellent yield. The synthetic route features good yield, transition metal-free and mild reaction conditions, and high tolerance for functionality, thereby allowing easy substitutions around the frutinone A core.
- Lei, Kang,Sun, Dong-Wei,Tao, Yuan-Yuan,Xu, Xiao-Hua
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- Preparation method of 4-substituted coumarin derivative under iron catalyst and basic additives
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The present invention relates to a manufacturing method of 4-substituted coumarin derivatives using iron catalysts and basic additives and, more specifically, to a method which ensures to manufacture 4-substituted coumarin derivatives having various functional groups at the position 4 with high yield in a short period of time while minimizing production of byproducts through a coupling reaction with a Grignard reagent by having 4-substituted coumarin sulfate as a starting material.COPYRIGHT KIPO 2015
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Paragraph 0079-0080; 0091-0094; 0097-0099
(2016/10/24)
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- Design, synthesis, and evaluation of 4-(substituted)phenyl-2-thioxo-3,4- dihydro-1H-chromino[4,3-d]pyrimidin-5-one and 4-(substituted)phenyl-3,4-dihydro- 1H-chromino[4,3-d]pyrimidine-2,5-dione analogs as antitubercular agents
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This paper focuses on the design and antitubercular activity of molecules which are a hybrid of coumarin and pyrimidine nuclei. A set of 16 compounds, viz. 4-(substituted) phenyl-3,4-dihydro-1H-chromino[4,3-d]pyrimidine-2,5-diones and 4-(substituted)phenyl-2-thioxo-3,4-dihydro-1H-chromino[4,3-d]pyrimidin-5- ones have been synthesized using green chemistry principles and evaluated for antitubercular activity by microplate Alamar blue assay (MABA) and lumi-nescence- based low oxygen-recovery assay (LORA) with rifampicin as the standard. The required Mycobacterium tuberculosis H37Rv strain for LORA was cultured using a plasmid bearing an acetamidase promoter driving a bacterial luciferase gene for signal enhancement and were allowed to adapt to low oxygen content in the fermenter. Compounds 5d, 5e, and 5g demonstratedmaximumantitubercular activity,with % inhibition values of 58, 55, and 45 based on MABA and 62, 35 and 37 based on the LORA tests at 128 μM. To understand the relationship between structure and activity, recursive partitioning (RP) models were developed. Two different RP models were built, one based on the antitubercular activity and the other based on the toxicity of the molecules. The decision tree could identify descriptors that discriminate the active and inactive as well as toxic and less toxic 3,4-annelated coumarin analogs. This RP model will be utilized in further work to design more potent molecules. Springer Science+Business Media 2013.
- Ambre, Premlata K.,Pissurlenkar, Raghuvir R. S.,Wavhale, Ravindra D.,Shaikh, Mushtaque S.,Khedkar, Vijay M.,Wan, Baojie,Franzblau, Scott G.,Coutinho, Evans C.
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p. 2564 - 2575
(2014/05/06)
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- Design and synthesis of 3,3′-biscoumarin-based c-Met inhibitors
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A library of biscoumarin-based c-Met inhibitors was synthesized, based on optimization of 3,3′-biscoumarin hit 3, which was identified as a non-ATP competitive inhibitor of c-Met from a diverse library of coumarin derivatives. Among these compounds, 38 and 40 not only showed potent enzyme activities with IC50 values of 107 nM and 30 nM, respectively, but also inhibited c-Met phosphorylation in BaF3/TPR-Met and EBC-1 cells. This journal is the Partner Organisations 2014.
- Xu, Jimin,Ai, Jing,Liu, Sheng,Peng, Xia,Yu, Linqian,Geng, Meiyu,Nan, Fajun
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p. 3721 - 3734
(2014/06/09)
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- Pd-catalyzed chemo-selective mono-arylations and bis-arylations of functionalized 4-chlorocoumarins with triarylbismuths as threefold arylating reagents
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Cross-coupling reactions of differently substituted 4-chlorocoumarins were studied under palladium catalysis using triarylbismuths as threefold arylating reagents. The high reactivity of 4-chlorocoumarins was demonstrated delivering mono- and bis-arylation products in a chemo-selective manner. The reaction conditions employed are simple, robust and the threefold coupling reactivity of triarylbismuth reagents was witnessed with good to high yields in 2-4 h conditions. The utility of the methodology was explored in the synthesis of a few natural occurring neoflavones (3.27-3.30). In addition, the 4-arylcoumarin 3.1 product is a useful precursor for the preparation of (R)-tolterodine.
- Rao, Maddali L.N.,Kumar, Abhijeet
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p. 6995 - 7005
(2015/03/14)
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- A new method for the facile synthesis of hydroxylated flavones by using allyl protection
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The iodine-induced oxidative cyclization of 2′-hydroxychalcones provides a simple, highly efficient approach to various hydroxy flavones and analogues. This process is run under mild conditions, tolerates various functional groups, and provides hydroxy flavones in good to excellent yield. The allyl-protected acetophenones and benzaldehydes were smoothly deallylated under similar conditions.
- Nawghare,Sakate,Lokhande
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p. 291 - 302
(2014/04/17)
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- Novel 2H-chromen derivatives: Design, synthesis and anticancer activity
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A series of novel dihydropyrazole derivatives linked with 2H-chromen were designed and synthesized. All of the compounds have been screened for their antiproliferative activity against MGC-803, Bcap-37, SGC-7901 and HepG 2 cell lines in vitro. The results revealed that compounds 4a and 10a exhibited strong inhibitory activity against HepG2 cell and manifested obvious un-toxic effect on GES-1 and L-02 cell lines. Some title compounds were tested against telomerase, compound 10a showed the most potent inhibitory activity with IC50 value at 0.98 ± 0.11 μM, it could fit well into the active site of TERT. The further molecular mechanism of antiproliferation was explored, the data suggested that compound 10a could inhibit hTERT expression and Wnt/β-catenin signaling.
- Qiang, Dong Zhi,Shi, Jing Bo,Song, Bao An,Liu, Xin Hua
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p. 5607 - 5617
(2014/01/23)
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- Synthesis and nematicidal bioevaluation of substituted 2H-1-benzopyrane-2- ones and their carbamate derivatives against root-knot nematode (Meloidogyne javanica)
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Synthesis of 7-hydroxy-4,5-methyl/7-hydroxy-4-methyl/7,8-dihydroxy-4- methyl/6-chloro-7-hydroxy-4-methyl-2H-1-benzopyrane-2-ones (VI-IX) have been carried out by Pechmann reaction. The condensation of synthesized 2H-1-benzopyran-2-ones (VI-X) with phenyl isocyanate (XI) gave 4,5-methyl/4-methyl/4-methyl/6-chloro-4-methyl-2-oxo-2H-benzopyran-7yl/7,8-diyl/ 4-yl/phenyl carbamates (XIIXVI). The synthesized compounds were characterized on the basis of analytical and spectral data. All the compounds were evaluated for their nematicidal activity in vitro against second stage juveniles (J2) of root-knot nematode (Meloidogyne javanica).
- Kumari, Sumona,Singh, Rajvir,Kumar, Anil,Walia
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p. 3139 - 3143
(2014/07/22)
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- Synthesis, anticancer activity and photophysical properties of novel substituted 2-oxo-2H-chromenylpyrazolecarboxylates
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2-Oxo-2H-chromenylpyrazolecarboxylates (8a-h and 12a-zb) have been synthesized by [3 + 2] cycloaddition of 2H-chromenophenylhydrazones (7a-h and 11a-w) with diethyl/dimethylbut-2-ynedioates. Phenylchromeno[4,3-c]pyrazol-4(1H) -ones (13i-n) were prepared from corresponding phenylhydrazones (7a-h) with catalytic amount of piperidine in presence of pyridine as a solvent at 100°C. All the synthesized compounds (8a-h, 12a-zb and 13a-n) were screened for anticancer activity against three human cancer cell lines such as prostate (DU-145), lung adenocarcinoma (A549), and cervical (HeLa) by standard MTT assay method. Further, photophysical properties (UV and fluorescence) for these compounds were discussed.
- Kumar, J. Ashok,Saidachary,Mallesham,Sridhar,Jain, Nishant,Kalivendi, Shashi Vardhan,Rao, V. Jayathirtha,Raju, B. China
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p. 389 - 402
(2013/10/01)
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- Palladium-catalyzed oxidative annulation via C-H/N-H functionalization: Access to substituted pyrroles
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Pyrroles, ubiquitous bioactive heterocycles in nature, are readily prepared via a palladium-catalyzed oxidative annulation of cyclic trans-enamines to various internal alkynes in the absence of a directing group. Copyright
- Peng, Shiyong,Wang, Lei,Huang, Jiayao,Sun, Shaofa,Guo, Haibing,Wang, Jian
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supporting information
p. 2550 - 2557
(2013/10/21)
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- Synthesis, characterization, and in vitro microbial evaluation of some new 4H-chromene and quinoline derivatives of 1H-pyrazole
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A new series of nine derivatives of 4H-pyrano[3,2-c]chromene and 12 derivatives of N-thiazolyl-4H-quinoline of 1H-pyrazole has been synthesized by one pot base catalyzed cyclocondensation reaction of 1H-pyrazole-4-carbaldehyde, malononitrile, and 4-hydroxy coumarin or β-enaminones, respectively. All the synthesized compounds were characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR spectral data and were further screened, against a panel of pathogenic strains of bacteria and fungi.
- Thumar, Nilesh J.,Patel, Manish P.
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p. 1169 - 1178
(2013/01/15)
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- Hydrazones derived from thiooxamohydrazides and 3-formyl-4-hydroxycoumarin: Synthesis, structures, and fragmentation
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Novel hydrazones were obtained from thiooxamohydrazides and 3-3-formyl-4-hydroxycoumarin. According to data from NMR spectroscopy and X-ray diffraction, the coumarin fragment in the compounds obtained exists as 4-hydroxycoumarin or chromane-2,4-dione. When dissolved in dimethyl sulfoxide, these hydrazones undergo fragmentation into derivatives of 1,3,4-thiadiazole and 4-hydroxycoumarin.
- Milevsky,Solov'Eva,Chibisova,Yarovenko,Zayakin,Chernyshev,Krayushkin,Traven
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p. 2311 - 2321
(2013/10/01)
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- Synthesis, antibacterial, and analgesic activity of novel 4-hydroxy-3-(phenylthio)-2H-chromen-2-ones and 4-Hydroxy-3-[imidazol/tetrazolo- 2-yl)thio]-2H-chromen-2-ones
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A mild and efficient synthesis of new 4-hydroxy-3-(phenylthio)-2H-chromen- 2-ones 4a-k and 4-hydroxy-3-[imidazol/tetrazolo-2-yl)thio]-2H-chromen-2-ones 6a-d is described. The compounds 4a-c were further subjected to oxidation by m-CPBA to obtain 3-(phenylsulfonyl)-4-hydroxy-2H-chromen-2-ones 5a-c. The structures of the resulted new compounds were established by IR, 1H NMR, mass, and elemental analysis. All the synthesized compounds were subjected to antibacterial activity against the Gram positive bacteria Staphylococcus aureus, Bacillus subtilis, and Streptococcus haemolytius and the Gram negative bacteria Salmonella typhi, Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumonia. The analgesic activity was carried out using Swiss albino male mice by abdominal concentration method. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright Taylor &Francis Group, LLC.
- Rajesha,Mahadevan, Kittappa M.,Satyanarayan,Bhojya Naik
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scheme or table
p. 1733 - 1743
(2011/10/08)
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