- Recyclable Copper Nanoparticles-Catalyzed Hydroboration of Alkenes and β-Borylation of α,β-Unsaturated Carbonyl Compounds with Bis(Pinacolato)Diboron
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Nano-ferrite-supported Cu nanoparticles (Fe-dopamine-Cu NPs) catalyzed anti-Markovnikov-selective hydroboration of alkenes with B2pin2 is reported under mild reaction conditions. This protocol can be applied to a broad range of substrates with high functional group compatibility. In addition, we demonstrated the use of Fe-dopamine-Cu NPs as a catalyst for the β-borylation of α,β-unsaturated ketones and ester, providing alkylboronate esters in up to 98% yield. Reuse of the magnetically recyclable catalyst resulted in no significant loss of activity in up to five reaction runs for both systems. (Figure presented.).
- Shegavi, Mahadev L.,Saini, Suresh,Bhawar, Ramesh,Vishwantha, Meghana Desai,Bose, Shubhankar Kumar
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supporting information
p. 2408 - 2416
(2021/03/16)
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- TRPV3 inhibitor and preparation method thereof
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The invention discloses a TRPV3 inhibitor which is formed by sequentially connecting an R1 group, an R group and an R2 group, and the molecular structural general formula of the TRPV3 inhibitor is shown as a formula 1 in the description. The invention als
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Paragraph 0169-0176
(2021/04/26)
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- The design and synthesis of transient receptor potential vanilloid 3 inhibitors with novel skeleton
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Transient receptor potential vanilloid 3 (TRPV3) channel as a member of thermo TRPV subfamily is primarily expressed in the keratinocytes of the skin and sensory neurons, and plays critical roles in various physiological and pathological processes such as
- Lv, Mengqi,Wu, Han,Qu, Yaxuan,Wu, Siyi,Wang, Junxia,Wang, Congcong,Luan, Yepeng,Zhang, Zhongyin
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- Fluorine as a robust balancer for tuning the reactivity of topo-photoreactions of chalcones and the photomechanical effects of molecular crystals
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Fluorine-free chalcones and chalcones bearing different numbers of fluorine atoms have been synthesized. It is found that fluorine can tune the reactivity of photo-induced [2 + 2] cycloaddition reactions in crystals. The higher the number of fluorine atom
- Gao, Hongqiang,Lu, Ran,Shu, Yuanhong,Sun, Jingbo,Wang, Haoran,Yang, Xiqiao,Ye, Kaiqi,Yue, Yuan,Zhong, Jiangbin
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p. 5856 - 5868
(2021/09/08)
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- Modular access to 1,2-allenyl ketones based on a photoredox-catalysed radical-polar crossover process
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Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developedviathe reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and allenation, the mechanism based on a photoredox-neutral-catalysed radical-polar crossover process has been proposed. Synthetic applications of allenes have also been demonstrated.
- Du, Chan,Fang, Jianghua,Fang, Yewen,Lei, Wan,Li, Yan,Liu, Yongjun
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supporting information
p. 8502 - 8506
(2021/10/20)
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- Pharmacophore hybridization approach to discover novel pyrazoline-based hydantoin analogs with anti-tumor efficacy
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In search for new and safer anti-cancer agents, a structurally guided pharmacophore hybridization strategy of two privileged scaffolds, namely diaryl pyrazolines and imidazolidine-2,4-dione (hydantoin), was adopted resulting in a newfangled series of compounds (H1-H22). Herein, a bio-isosteric replacement of “pyrrolidine-2,5-dione” moiety of our recently reported antitumor hybrid incorporating diaryl pyrazoline and pyrrolidine-2,5-dione scaffolds with “imidazoline-2,4-dione” moiety has been incorporated. Complete biological studies revealed the most potent analog among all i.e. compound H13, which was at-least 10-fold more potent compared to the corresponding pyrrolidine-2,5-dione, in colon and breast cancer cells. In-vitro studies showed activation of caspases, arrest of G0/G1 phase of cell cycle, decrease in the expression of anti-apoptotic protein (Bcl-2) and increased DNA damage. In-vivo assay on HT-29 (human colorectal adenocarcinoma) animal xenograft model unveiled the significant anti-tumor efficacy along with oral bioavailability with maximum TGI 36% (i.p.) and 44% (per os) at 50 mg/kg dose. These findings confirm the suitability of hybridized pyrazoline and imidazolidine-2,4-dione analog H13 for its anti-cancer potential and starting-point for the development of more efficacious analogs.
- Upadhyay, Neha,Tilekar, Kalpana,Loiodice, Fulvio,Anisimova, Natalia Yu.,Spirina, Tatiana S.,Sokolova, Darina V.,Smirnova, Galina B.,Choe, Jun-yong,Meyer-Almes, Franz-Josef,Pokrovsky, Vadim S.,Lavecchia, Antonio,Ramaa
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- Design, synthesis, and SAR study of novel 4,5-dihydropyrazole-Thiazole derivatives with anti-inflammatory activities for the treatment of sepsis
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Systemic inflammatory response syndrome is a major feature of sepsis which is one of the major causes of death worldwide. It has been reported that 3,5-diaryl-4,5-dihydropyrazole and thiazole derivatives have many biological functions, especially in the aspect of anti-inflammation. According to the strategy of pharmacophore combination, we introduced thiazole moiety into dihydropyrazole skeleton to design and synthesize a novel series of 2-(3,5-diphenyl-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole derivatives, and evaluated their anti-inflammatory activities for sepsis treatment. Preliminary structure?activity relationship (SAR) analysis was conducted by their inhibitory activities against nitric oxide (NO) release in LPS-induced RAW264.7 cells, and the optimal compound E26 exhibited more potent anti-inflammatory activity than the positive control treatment indomethacin and dexamethasone. In further mechanism study, our results showed that compound E26 significantly suppressed the production of interleukin-1β (IL-1β), tumor necrosis factor-α (TNF-α), NO and inhibited the expressions of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2) through blocking MAPKs signaling pathway. In addition, in vivo administration of compound E26 resulted in a significant improvement of LPS-induced sepsis in C57BL/6J mice, with reducing toxicity in multiple organs. Taken together, this study demonstrated the compound E26 could be a promising agent for the treatment of sepsis.
- Cao, Peichang,Duan, Yajun,Fang, Mengyuan,Han, Jihong,Li, Qing-Shan,Xu, Huajian,Yang, Xiaoxiao,Zhang, Zhen,Zou, Tingfeng
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- Bu4NHSO4-Catalyzed Direct N-Allylation of Pyrazole and its Derivatives with Allylic Alcohols in Water: A Metal-Free, Recyclable and Sustainable System
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Allylic amines are valuable and functional building blocks. Direct N-allylation of pyrazole and its derivatives as an atom economic strategy to provide allylic amines has been achieved only using commercial Bu4NHSO4 as the metal-free catalyst and water as the solvent without any additives. 11–93% isolated yields were obtained for the N-allylation of pyrazole and its derivatives with allylic alcohols. Bu4NHSO4 could be reused for six times by simple extraction nearly without loss of catalytic activity and was also suitable for a gram-scale production. The reaction of allylic ether and pyrazole did not occur to give the desired product indicated that allylic ether was not the active intermediate in the pathway. Density functional theory (DFT) calculations reveal that there are hydrogen bonding effects among substrates, solvent and catalyst, especially the one formed between allylic alcohol and H2O. Control experiments in different protic solvents further demonstrate the intermolecular hydrogen bonding of allylic alcohol and water. (Figure presented.).
- Zhuang, Hongfeng,Lu, Nan,Ji, Na,Han, Feng,Miao, Chengxia
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supporting information
p. 5461 - 5472
(2021/09/29)
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- Multi-target weapons: diaryl-pyrazoline thiazolidinediones simultaneously targeting VEGFR-2 and HDAC cancer hallmarks
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In anticancer drug discovery, multi-targeting compounds have been beneficial due to their advantages over single-targeting compounds. For instance, VEGFR-2 has a crucial role in angiogenesis and cancer management, whereas HDACs are well-known regulators o
- C S, Ramaa,Kumar, Alan P.,Meyer-Almes, Franz-Josef,Safuan, Sabreena,Schweipert, Markus,Tilekar, Kalpana,Upadhyay, Neha
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p. 1540 - 1554
(2021/10/26)
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- Double-edged Swords: Diaryl pyrazoline thiazolidinediones synchronously targeting cancer epigenetics and angiogenesis
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In the present study, two novel series of compounds incorporating naphthyl and pyridyl linker were synthesized and biological assays revealed 5-((6-(2-(5-(2-chlorophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethoxy) naphthalene-2-yl)methylene)thiazolidine-2,4-dione (14b) as the most potent dual inhibitors of vascular endothelial growth factors receptor-2 (VEGFR-2) and histone deacetylase 4 (HDAC4). Compounds 13b, 14b, 17f, and 21f were found to stabilize HDAC4; where, pyridyl linker swords were endowed with higher stabilization effects than naphthyl linker. Also, 13b and 14b showed best inhibitory activity on VEGFR-2 as compared to others. Compound 14b was most potent as evident by in-vitro and in-vivo biological assessments. It displayed anti-angiogenic potential by inhibiting endothelial cell proliferation, migration, tube formation and also suppressed new capillary formation in the growing chick chorioallantoic membranes (CAMs). It showed selectivity and potency towards HDAC4 as compared to other HDAC isoforms. Compound 14b (25 mg/kg, i.p.) also indicated exceptional antitumor efficacy on in-vivo animal xenograft model of human colorectal adenocarcinoma (HT-29). The mechanism of action of 14b was also confirmed by western blot.
- Kumar, Alan P.,Meyer-Almes, Franz-Josef,Ramaa, C. S.,Safuan, Sabreena,Schweipert, Markus,Tilekar, Kalpana,Upadhyay, Neha
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- Synthesis and theoretical study of a series of 3,5-disubstitutes pyrazoles
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In this work, we proposed the synthesis of a series of pyrazoles derivatives with different substituents on the aromatic rings. We aim to evaluate their influence on the reactivity of the compounds in reactions of α,β-unsaturated chalcones and sulfonyl hydrazide catalyzed by iodine. In order to explain their high and low yields, or the impossibility of obtaining some compounds by applied synthetic methodology, Density Functional Theory (DFT) calculations were performed. The reaction Gibbs free energy (ΔG) as well as the energy gap of the HOMO-LUMO frontier orbitals (ΔE) of some selected reactants could explain qualitatively the experimental observations in terms of synthesis yield. In this way, we believe that the chemical nature of aromatic ring substituents is relevant for the reactivity of the starting materials as well as the formation of the desired products.
- Branco, Ana Clara Alves,Couri, Mara Rubia Costa,Enes, Karine Braga,Guimar?es, Luciana,Lima, Maria Eduarda Toledo,Mateus, Marcella Fernandes Mano,Nascimento, Clebio Soares
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p. 932 - 938
(2020/12/23)
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- Discovery of Novel Approach for Regioselective Synthesis of Thioxotriaza-Spiro Derivatives via Oxalic Acid
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A vital approach for the synthesis of a range of novel thioxotriaza-spiro derivatives is described. These new heterocyclic systems are obtained via oxalic acid catalyzed reaction of α,β-unsaturated ketones in the presence of 5,6-diamino-2-mercaptopyrimidi
- Gopinatha, Vindya K.,Mantelingu, Kempegowda,Raghavan, Sathees C.,Rangappa, Kanchugarakoppal S.,Swarup, Hassan A.
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supporting information
p. 2004 - 2009
(2019/10/28)
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- Synthesis and bioevaluation of thienopyrimidines bearing a pyrazoline unit as selective PI3Kα inhibitors
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A series of thienopyrimidines containing a pyrazoline unit (4a-d, 7a-d and 13a-l) were designed and synthesized. The target compounds were evaluated for antiproliferative activity against A549, HepG2 and MCF-7 cancer cell lines. Among the twenty target compounds, most of them exhibited excellent antiproliferative activity against one or several cancer cell lines. Compound 13f showed the best activity against A549, MCF-7 and HepG2 cancer cell lines, with IC50 values of 2.84 ± 0.09 μM, 2.88 ± 0.43 μM and 2.08 ± 0.36 μM, respectively. Four selected compounds (13c, 13f, 13g and 13h) were further evaluated for their inhibitory activity against the PI3Kα/mTOR protein kinase. Moreover, time-dependent and dose-dependent experiments, AO fluorescence staining, Annexin V-FITC/PI staining and docking studies were carried out in this study. The results indicated that compound 13f may be a potential selective PI3Kα inhibitor.
- Lai, Luogen,Wang, Qinqin,Zhang, Binliang,Xiao, Zhen,Yang, Zunhua,Yang, Qi,Luo, Zixin,Zhu, Wufu,Xu, Shan
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p. 29579 - 29589
(2019/10/01)
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- Design, synthesis, and biological evaluation of novel thienopyrimidine derivatives as PI3Kα inhibitors
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Three series of novel thienopyrimidine derivatives 9a-l, 15a-l, and 18a-h were designed and synthesized, and their IC50 values against four cancer cell lines HepG-2, A549, PC-3, and MCF-7 were evaluated. Most compounds show moderate cytotoxicity against the tested cancer cell lines. The most promising compound 9a showed moderate activity with IC50 values of 12.32 ± 0.96, 11.30 ± 1.19, 14.69 ± 1.32, and 9.80 ± 0.93 μM, respectively. The inhibitory activities of compounds 9a and 15a against PI3Kα and mTOR kinase were further evaluated. Compound 9a exhibited PI3Kα kinase inhibitory activity with IC50 of 9.47 ± 0.63 μM. In addition, docking studies of compounds 9a and 15a were also investigated.
- Yu, Lide,Wang, Qinqin,Wang, Caolin,Zhang, Binliang,Yang, Zunhua,Fang, Yuanying,Zhu, Wufu,Zheng, Pengwu
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- A catalytic allylic cation-induced intermolecular allylation-semipinacol rearrangement
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A catalytic intermolecular semipinacol rearrangement induced by allylic carbocations has been realized. This tandem reaction is highly efficient under the catalysis of ZnBr2, generating a wide range of α-homoallyl substituted ketones which contain all-carbon quaternary centres in good to excellent yields (up to 98%) with moderate to high diastereoselectivities (up to >20?:?1). Synthetic application of this novel methodology in the construction of core structures of natural products is also reported.
- Xu, Ming-Hui,Dai, Kun-Long,Tu, Yong-Qiang,Zhang, Xiao-Ming,Zhang, Fu-Min,Wang, Shao-Hua
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supporting information
p. 7685 - 7688
(2018/07/15)
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- Synthesis of symmetrical and unsymmetrical triarylpyrylium ions: Via an inverse electron demand Diels-Alder reaction
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BF3·OEt2 mediated inverse electron demand Diels-Alder (IEDDA) reaction of chalcones with aryl acetylenes is reported for the synthesis of symmetrical and unsymmetrical 2,4,6-triarylpyrylium ions. The protocol provides an effective one-pot method for the utilization of readily available simple substrates under mild reaction conditions leading to a diverse array of pyrylium ions in moderately good yield.
- Fathimath Salfeena,Basavaraja,Ashitha,Kumar, V. Praveen,Varughese, Sunil,Suresh, Cherumuttathu H.,Sasidhar
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supporting information
p. 12463 - 12466
(2018/11/20)
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- Synthesis and biological evaluation of coumarin clubbed thiazines scaffolds as antimicrobial and antioxidant
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A new series of 4-methyl-6-nitro-2-oxo-2H-chroman-7yl-2-(4-(4-fluorophenyl)-6-phenyl-2H-1,3-thiazin-2-yl-amino)acetates 5a–j were synthesized from 6-nitro-4-methyl coumarinyl chloroacetate (5) and 2-amino thiazines (IIIa–j). The structure of the final compounds was adequately confirmed via spectroscopic techniques (IR, 1H NMR, 13C NMR, Mass) and characterization of physical properties. Final compounds were screened for their antimicrobial, antitubercular, and antioxidant activities. Compounds 5c and 5h found to have antibacterial potency against E. coli with MIC values 50 μg/mL compared to standard drugs. Compound 5d demonstrated better antifungal potency (MIC = 200 μg/mL) against C. albicans when compared with griseofulvin. Compounds 5b and 5h found to be encouraging antitubercular (MIC = 62.5 μg/mL with 98–99% inhibition) against M. tuberculosis H37Rv. The newly synthesized 5h and 5b were appeared to have high radical scavenging efficacies as 33.99 ± 0.301 and 35.35 ± 0.470 μg/mL ± SD of IC50 values, respectively, in DPPH and ABTS bioassay.
- Chauhan, Nilesh B.,Patel, Navin B.,Patel, Vatsal M.,Mistry, Bhupendra M.
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p. 2141 - 2149
(2018/07/21)
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- Direct Reduction of Allylic Alcohols Using Isopropanol as Reductant
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The lithium cation-catalyzed direct reduction of allylic alcohols to alkenes using isopropanol as a hydride donor was developed. The hydride transfer of the in situ-generated lithium isopropoxide to an allylic cation is the key process in this transformation. The reaction generates only water and acetone as byproducts, which highlights the synthetic utility of this method. (Figure presented.).
- Sai, Masahiro
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supporting information
p. 3482 - 3487
(2018/09/14)
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- Synthesis, spectral, biological activity, and crystal structure evaluation of novel pyrazoline derivatives having sulfonamide moiety
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In the present study, synthesis and characterization of pyrazoline derivatives integrated with sulfonamide scaffold have been performed. The characterization of the molecules was done by elemental analysis, ultraviolet–visible, infrared, nuclear magnetic
- Sadashiva, Rajitha,Naral, Damodara,Kudva, Jyothi,Shivalingegowda, Naveen,Lokanath, Neratur Krishnappagowda,Pampa, Kudigana Jayaprakash
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p. 1213 - 1227
(2017/05/04)
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- Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols
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Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols provides chalcones and benzyl styrenes. The use of various metal triflates is investigated herein for facile and efficient redox transformation. A plausible mechanism has been proposed.
- Chan, Chieh-Kai,Tsai, Yu-Lin,Chang, Meng-Yang
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p. 3368 - 3376
(2017/05/22)
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- Synthesis and structure-activity relationships of 4-morpholino-7,8-dihydro-5h-thiopyrano[4,3-d] pyrimidine derivatives bearing pyrazoline scaffold
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Phosphatidylinositol 3-kinase/Protein kinase B/Mammalian target of rapamycin (PI3K/Akt/mTOR) signaling pathway is abnormally active in the growth and proliferation of cancer cells. The inhibition of PI3K kinase can effectively block the conduction of sign
- Wang, Qinqin,Li, Xiaojing,Sun, Chengyu,Zhang, Binliang,Zheng, Pengwu,Zhu, Wufu,Xu, Shan
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-
- Transition-Metal-Free Synthesis of Homo- and Hetero-1,2,4-Triaryl Benzenes by an Unexpected Base-Promoted Dearylative Pathway
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An unprecedented approach for the synthesis of homo- and hetero-1,2,4-triaryl benzenes has been developed using a simple base-mediated reaction of either α-aryl cinnamyl alcohols or α,γ-di-aryl propanones. The salient feature of this strategy involves the sequential hydride transfer, regiospecific condensation, regiospecific dearylation, and aromatization under metal-free reaction conditions. The synthesis of unsymmetrically substituted triphenylenes by oxidative coupling of the synthesized 1,2,4-triaryl benzenes has also been demonstrated.
- Rehan, Mohammad,Maity, Sanjay,Morya, Lalit Kumar,Pal, Kaushik,Ghorai, Prasanta
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supporting information
p. 7728 - 7732
(2016/07/07)
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- Synthesis, molecular docking study, and cytotoxic activity of 1,3,5-triaryl pyrazole derivatives
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Synthesis, molecular docking study, and cytotoxic activity of a new group of 1,3,5-triaryl pyrazole derivatives were be studied. The antiproliferative activity of the final compounds were examined in MCF-7, AGS, HT-29 and NIH3T3 cell lines by MTT assay, u
- Ghasemi, Maryam,Ghadbeighi, Sajad,Amirhamzeh, Amirali,Tabatabai, Seyed Abbas,Ostad, Seyed Nasser,Shafiee, Abbas,Amini, Mohsen
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p. 121 - 128
(2016/03/12)
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- Heteroleptic ruthenium(II) polypyridine complexes with a series of substituted 2,2′-bipyridine ligands
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Five substituted-2,2′-bipyridine ligands L, (4-(p-methylphenyl)-6-phenyl-2,2′-bipyridine (L1), 4-(p-bromophenyl)-6-(p-bromophenyl)-2,2′-bipyridine (L2), 4-(p-bromophenyl)-6-phenyl-2,2′-bipyridine (L3), 4-phenyl-6-(p-bromophenyl)-2,2′-bipyridine (L4), and 4-(p-fluorophenyl)-6-(p-fluorophenyl)-2,2′-bipyridine (L5) were synthesized by stepwise formation. Reaction of cis-[RuCl2(bpy)2]2H2O or cis-[RuCl2(phen)2]2H2O and the substituted-2,2′-bipyridine ligands in the presence of KPF6 afforded the corresponding cationic polypyridine-ruthenium complexes of the type [(bpy)2Ru(L)](PF6)2 (bpy = 2,2′-bipyridine, 1-5) or [(phen)2Ru(L)](PF6)2 (phen = 1,10-phenanthroline, 6-10), respectively. All complexes have been spectroscopically characterized by UV-vis, luminescence, and electrogenerated chemiluminescence. The structures of 1CH3COCH3, 3CH3COCH3, 52CH3COCH3, 6, 8, 9, and 10 have been determined by single-crystal X-ray diffraction.
- Wang, Zhi-Min,Shen, Su-Mei,Shen, Xiu-Yin,Xu, Ya-Qin,Jia, Ai-Quan,Zhang, Qian-Feng
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p. 851 - 861
(2016/04/04)
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- Substituent-Controlled Chemoselective Cleavage of C = C or Csp2 - C(CO) Bond in α,β-Unsaturated Carbonyl Compounds with H-Phosphonates Leading to β-Ketophosphonates
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An unprecedented substituent-controlled chemoselective cleavage of C = C double bond or C(sp2)-C(CO) bond along with aerobic phosphorylation of α,β-unsaturated carbonyl compounds with H-phosphonates through a radical process has been disclosed. The current strategy provides an access to β-ketophosphonates under mild conditions with a wide substrate scope.
- Zhou, Yao,Rao, Changqing,Mai, Shaoyu,Song, Qiuling
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p. 2027 - 2034
(2016/03/15)
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- Mild and efficient reductive deoxygenation of epoxides to olefins with tin(II) chloride/sodium iodide as a novel reagent
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A highly efficient and green protocol is reported for the reductive deoxygenation of organic epoxides to olefins using tin(II) chloride/sodium iodide as a novel reagent. The reaction gives an excellent yield (85-96%) in ethanol under reflux within 2-10 minutes, without affecting other functional groups. The advantages of our method are the use of inexpensive reagents, the eco-friendly and green reaction conditions, and the short reaction times and high yields.
- Pathe, Gulab Khushalrao,Ahmed, Naseem
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supporting information
p. 3542 - 3552
(2015/11/17)
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- ANTI-INVASIVE COMPOUNDS
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The present invention relates to the field of anti-invasive compounds and methods for predicting the anti-invasive activity of said compounds, as well as their use in the prevention and/or treatment of diseases associated with undesired cell invasion; in particular, this invention relates to the field of anti-invasive chalcone-like compounds.
- -
-
Paragraph 0361-0363; 0369-0372
(2015/02/18)
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- 4-Fluoro-3′,4′,5′-trimethoxychalcone as a new anti-invasive agent. From discovery to initial validation in an in vivo metastasis model
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Invasion and metastasis are responsible for 90% of cancer-related mortality. Herein, we report on our quest for novel, clinically relevant inhibitors of local invasion, based on a broad screen of natural products in a phenotypic assay. Starting from micromolar chalcone hits, a predictive QSAR model for diaryl propenones was developed, and synthetic analogues with a 100-fold increase in potency were obtained. Two nanomolar hits underwent efficacy validation and eADMET profiling; one compound was shown to increase the survival time in an artificial metastasis model in nude mice. Although the molecular mechanism(s) by which these substances mediate efficacy remain(s) unrevealed, we were able to eliminate the major targets commonly associated with antineoplastic chalcones.
- Roman, Bart I.,De Ryck, Tine,Patronov, Atanas,Slavov, Svetoslav H.,Vanhoecke, Barbara W.A.,Katritzky, Alan R.,Bracke, Marc E.,Stevens, Christian V.
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supporting information
p. 627 - 639
(2015/08/03)
-
- Synthesis and anticancer activity of 1,3,5-triaryl-1H-pyrazole
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Previous studies demonstrated that some pyrazole derivatives could be considered as potential anticancer agents. A series of 1,3,5-triaryl-1H-pyrazole derivatives were prepared by the reaction of phenylhydrazin and different chalcones. The previous classi
- Ghadbeigi, Sajad,Ostad, Seyed Nasser,Shafiee, Abbas,Amini, Mohsen
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p. 754 - 759
(2015/10/05)
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- Copper-catalyzed oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles
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A mild and convenient oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles is uncovered by employing trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of a catalytic amount of copper(II) perchlorate hexahydrate [Cu(ClO4)2 .6 H2O] (5 mol%) and 2,3-dichloro-5,6-dicyano-para- benzoquinone (DDQ) (1.2 equiv.) as an oxidant. This reaction is performed under ambient conditions and proceeds through C-C bond cleavage.
- Rokade, Balaji V.,Gadde, Karthik,Prabhu, Kandikere Ramaiah
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supporting information
p. 946 - 950
(2014/04/03)
-
- Electronically tunable anion-π interactions in pyrylium complexes: Experimental and theoretical studies
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Noncovalent interactions of anions with electron-deficient aromatic rings that have been studied so far involve non-heteroaromatic or nitrogen-based heteroaromatic systems. Here we report the first case of an organic oxygenated aromatic system, in particular the tri-aryl-pyrylium tetrafluoroborate system, for which noncovalent anion-π interactions of the pyrylium cation with the tetrafluoroborate anion have been experimentally detected and demonstrated by means of 19F NMR spectroscopy in solution. A series of pyrylium tetrafluoroborate salts were synthesized in the presence of BF 3·Et2O, by direct reaction of 4-substituted benzaldehydes with 4-substituted acetophenones or via the previously obtained chalcone of the less reactive ketone. Correlations of 19F NMR chemical shifts of tetrafluoroborate anion for most of the synthesized tri-arylpyrylium tetrafluoroborate complexes with both the pyrylium cation molecular weight and the standard substituent Hammett constants, demonstrate anion-π+ interaction to act between the polyatomic anion BF 4- and the pyrylium aromatic system. DFT calculations reveal that an additional (C-H)+-anion hydrogen bond involving the H(5) of pyrylium ring exists for these fluorescent dyes that show a tunable cup-to-cap shape cavity. The strong fluorescence emission observed for some representative pyrylium tetrafluoroborates described herein, makes them a promising class of tunable emission wavelength dyes for laser technology applications. the Partner Organisations 2014.
- Franconetti, Antonio,Contreras-Bernal, Lidia,Jatunov, Sorel,Gomez-Guillen, Manuel,Angulo, Manuel,Prado-Gotor, Rafael,Cabrera-Escribano, Francisca
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p. 18442 - 18453
(2014/10/15)
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- An efficient simple one-pot synthesis, characterization and structural studies of some 1,2,3,5-tetraarylpentane-1,5-diones
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A series of 1,2,3,5-tetraarylpentane-1,5-diones (9-23) were synthesised by simple one-pot method and characterized by FT-IR, 1H NMR, 13C NMR and mass spectral techniques. The structure of 3-(4-fluorophenyl)-1,2,5-triphenylpentane-1,5-dione (10) was determined by single crystal X-ray diffraction analysis. The compound 10 crystallize in monoclinic crystal system, in C2/c space group. The torsional angle between the two keto groups was found to be -29.50. The C(23)C(22)C(15)C(8)C(7) chain is almost planar with "W" conformation and observed maximum deviation is 0.122 ? for C(15) from the C(23)/C(22)/C(15)/C(8)/C(7) plane.
- Senthilkumar,Neelakandan,Manikandan
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- A facile microwave-assisted "one-Pot" synthesis of piperazino pyrimidinyl acetamides, a class of hybrid bis heterocycles and their structural elucidation using NMR spectral techniques
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An array of novel piperazino pyrimidinyl acetamides, a class of hybrid bis heterocycles are synthesized in "one-pot" by microwave irradiation method catalyzed by heterogeneous NaHSO4.SiO2 catalyst in dry media and are characterized by melting point, elemental analysis, MS, FT-IR, one-dimensional NMR (1H and 13C) and two-dimensional 1H-1H COSY and 1H-13C HSQC spectral data.
- Kanagarajan,How, Ghee Ang,Siu, Choon Ng,Gopalakrishnan
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p. 396 - 402
(2013/05/23)
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- An improved iron-mediated synthesis of N-2-aryl substituted 1,2,3-triazoles
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Treatment of various chalcones and sodium azide in the presence of catalytic amounts of commercially available iron oxide nanoparticles, followed by the addition of aryl halides afforded N-2-arylated 1,2,3-triazoles in very good yields. This tandem three-
- Kamal, Ahmed,Swapna, Ponnampalli
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p. 7419 - 7426
(2013/06/27)
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- Synthesis and biological evaluation of some new 4-aryl-1-(4,6-diaryl pyrimidine)-2-azetidinone by conventional and microwave methods and their biological activities
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4-Aryl-1-(4,6-diaryl pyrimidine)-2-azetidinone/4-aryl-3-chloro-1-(4,6- diaryl pyrimidine)-2-azetidinone were prepared by reaction of appropriate 2-(methoxy phenylideneamino)-4-diaryl pyrimidine (Schiff base) and acetyl chloride/chloroacetylchloride in dim
- Sharma, Sharda,Jain, Renuka,Sharma, Vikas,Chawla, Chetali
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p. 221 - 229
(2013/06/04)
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- Design, synthesis and biological evaluation of pyrazolyl-thiazolinone derivatives as potential EGFR and HER-2 kinase inhibitors
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A series of pyrazolyl-thiazolinone derivatives (E1-E36) have been designed and synthesized and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors. Thirty-four of the 36 compounds were reported for the first time. Among them, compound 2-(5-(4-bromophenyl)-3-p-tolyl-4,5- dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (E28) displayed the most potent inhibitory activity (IC50 = 0.24 μM for EGFR and IC50 = 1.07 μM for HER-2). Antiproliferative assay results indicated that compound E28 owned high antiproliferative activity against MCF-7, B16-F10 and HCT-116 in vitro, with IC50 value of 0.30, 0.54, and 0.70 μM, respectively. Docking simulation was further performed to position compound E28 into the EGFR active site to determine the probable binding model. Based on the preliminary results, compound E28 with potent inhibitory activity in tumor growth would be a potential anticancer agent.
- Qiu, Ke-Ming,Wang, Hai-Hong,Wang, Li-Ming,Luo, Yin,Yang, Xian-Hui,Wang, Xiao-Ming,Zhu, Hai-Liang
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experimental part
p. 2010 - 2018
(2012/05/04)
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- Iron-oxide nanoparticles mediated cyclization of 3-(4-chlorophenyl)-1- hydrazinylisoquinoline to 1-(4,5-dihydropyrazol-1-yl)isoquinolines
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Iron-oxide nanoparticles were obtained using chitosan templates and their crystalline character and particle size have been confirmed through powder x-ray diffraction and transmission electron microscopy measurements. The particle sizes were found to be 10-25 nm. The diversified chalcones 2 were reacted with 1-hydrazinylisoquinoline 1 in the presence of iron-oxide nanoparticles to the corresponding pyrazolines 3a-j in high yield and purity. The pyrazolines were characterized by spectroscopic techniques. Springer Science+Business Media B.V. 2011.
- Nawaz Khan,Manivel,Prabakaran,Jin, Jong Sung,Jeong, Euh Duck,Kim, Hyun Gyu,Maiyalagan
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experimental part
p. 571 - 582
(2012/06/01)
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- Antimicrobial, analgesic, DPPH scavenging activities and molecular docking study of some 1,3,5-triaryl-2-pyrazolines
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A series of 1,3,5-triaryl-2-pyrazolines 2a-g were synthesized by the reaction of 4,40-disubstituted chalcone with phenyl hydrazine. All these compounds were characterized by NMR, IR and mass spectral and single crystal XRD data. All the synthesized produc
- Samshuddin, Seranthimata,Narayana, Badiadka,Sarojini, Balladka Kunhanna,Raj, Chenna Govindaraju Darshan,Khan, Mahmud Tareq Hassan,Yathirajan, Hemmige S.,Raghavendra, Ramappa
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p. 2012 - 2022,11
(2020/07/30)
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- Synthesis of some novel benzofuran-2-yl(4,5-dihyro-3,5-substituted diphenylpyrazol-1-yl) methanones and studies on the antiproliferative effects and reversal of multidrug resistance of human MDR1-gene transfected mouse lymphoma cells in vitro
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A new series of benzofuran-2-yl(4,5-diydro-3,5-substituted diphenylpyrazol-1-yl) methanone derivatives 8a-x by the reaction of the benzofuran-2-carbohydrazides 7 with various chalcone derivatives 3a-x using microwave irradiation has been described. The effect of synthesized compounds 8a-v was studied against human cancer cell lines for their antiproliferative activity and reversal of multidrug resistance on human MDR1-gene transfected mouse lymphoma cells. Among the 24 compounds, the 8c and 8h showed good antiproliferative activity 8b, 8f and 8k were exhibited good MDR reversal activity. The main significance of the process is easy workup process, short reaction time and high yield of the new compounds for biological interest. However, the studies on genetically modified multidrug resistant cancer cells are costly and time consuming.
- Parekh, Shrey,Bhavsar, Dhairya,Savant, Mahesh,Thakrar, Shailesh,Bavishi, Abhay,Parmar, Manisha,Vala, Hardevsinh,Radadiya, Ashish,Pandya, Nilay,Serly, Juliana,Molnár, Joseph,Shah, Anamik
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scheme or table
p. 1942 - 1948
(2011/04/26)
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- Synthesis and in vitro microbiological evaluation of an array of biolabile 2-morpholino-N-(4,6-diarylpyrimidin-2-yl)acetamides
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Biolabile 2-morpholino-N-(4,6-diarylpyrimidin-2-yl)acetamides 34-42 have been synthesized and evaluated for their in vitro antibacterial and antifungal activities. The minimum inhibitory concentration tested for the same compounds against the same set of bacterial and fungal strains shows that the compounds 36 and 38 against β-Heamolytic streptococcus and Klebsiella pneumonia, 40 against Escherichia coli and Pseudomonas, have excellent antibacterial activity. Compounds 36, 38 and 42 show inhibition against Aspergillus flavus, compound 41 against Microsporum gypsuem, 42 against Mucor, and compounds 39 and 40 against Rhizopus.
- Kanagarajan,Thanusu,Gopalakrishnan
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scheme or table
p. 1583 - 1589
(2010/06/12)
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- Design, synthesis and spectral characterization of novel 2-morpholino-n-(4,6-diarylpyrimidin-2-yl)acetamides
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A new series of novel 2-morpholino-N-(4,6-diarylpyrimidin-2-yl)acetamides 34-42 is synthesized by the condensation of 2-chloro-N-(4,6-diarylpyrimidin-2- yl)acetamides 25-33 with morpholine in the presence of anhydrous potassium carbonate. The synthesized compounds have been characterized by melting point, elemental analysis, MS, FT-IR, one-dimensional NMR (1H & 13C) spectroscopic data.
- Kanagarajan, Vijayakumar,Thanusu, Jayaraman,Gopalakrishnan, Mannathusamy
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scheme or table
p. 49 - 54
(2010/09/05)
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- Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity
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The α-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G2/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 μM; CA4, 0.10 μM) and compete with [3H]colchicine for binding to tubulin (8% [3H]colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity.
- Ducki, Sylvie,Rennison, David,Woo, Meiko,Kendall, Alexander,Chabert, Jeremie Fournier Dit,McGown, Alan T.,Lawrence, Nicholas J.
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supporting information; experimental part
p. 7698 - 7710
(2010/03/24)
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- Base catalyzed formation and ring cleavage of 2- acyl-4- alkoxycarbonyl- 4-cyano substituted cyclohexanoles
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THE REACTION of 1,3-diaryl-2-propen-1-ones (1a,b) with ethyl cyanoacetate in absolute ethanol in the presence of a catalytic amount of KOH at 50-55 °C afforded 3-aroyl-1-cyano-4-hydroxy-2,4, 6-triarylcyclohexanecarboxylates (2a,b). Base-catalyzed ring cleavage of 2a,b in refluxing ethanolic KOH solution afforded the corresponding 3-aryl- 2-cyano-2-propenoic acid 4 along with 1a,b. The structure of 2 was established through different spectroscopic techniques and confirmed via dehydration using thionyl chloride in refluxing pyridine afforded 3. However, reaction of 1a with ethyl cyanoacetate in refluxing ethanol in the presence of secondary amine (piperidine or morpholine) as a basic catalyst gave the open-chain Michael adduct 6. Treatment of the latter with ethanolic KOH solution yielded 1,5-pentanedione derivative 7. The relative configurations of 3b and 6 were determined through single crystal X-ray diffraction analysis.
- Mishriky,Girgis,Ahmed-Farag
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experimental part
p. 249 - 264
(2012/04/23)
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- Stabilization of ketone and aldehyde enols by formation of hydrogen bonds to phosphazene enolates and their aldol products
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Solution properties of enolates generated using the phosphazene (Schwesinger) base P4-tBu were investigated by NMR spectroscopy. With a full equivalent of base the benzyl ketones 1a and 1b, the acetophenone 2, the arylacetaldehyde 1c, and the methyl arylacetate 1d formed the expected "naked" (P4H+) enolates 3 and 7. However, at a half-equivalent of base the ketones 1a and 1b as well as the aldehyde 1c formed solutions of stable hydrogen-bonded dimeric (enol-enolate) structures (4). The acetophenone 2, on the other hand, forms only traces of the H-bonded dimer 8 during deprotonation of 2. The thermodynamic product was the isomeric self-aldol condensation product 12. The mechanism of this condensation was elucidated by low temperature rapid-injection (RI) NMR spectroscopy. Solutions of 8 stable enough for NMR characterization could be transiently generated by semiprotonation of the enolate 7 with HCl·OEt2 at -130 °C using RINMR. The ester enolate 1d gave no trace of 4d even on a time scale as short as a few seconds at -130 °C either during the semideprotonation of 1d, or during semiprotonation of the enolate 3d. Long-lived solutions of the enols derived from 1a, 1b, 1c, and 2 (but not 1d) could be produced by full protonation of the phosphazene enolates with HCl·OEt2 at low temperature. Copyright
- Kolonko, Kristopher J.,Reich, Hans J.
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supporting information; experimental part
p. 9668 - 9669
(2009/02/04)
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- Monoamine oxidase isoform-dependent tautomeric influence in the recognition of 3,5-diaryl pyrazole inhibitors
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A series of 3,5-diaryl pyrazoles were prepared and assayed for their ability to inhibit reversibly monoamine oxidase-A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds show inhibitory activity with concentration values in the nanomolar range. A computational work was carried out on the two most selective inhibitors that have tautomeric pyrazole forms. The binding free energies of these compounds for each MAO isoform were influenced by the tautomeric equilibria.
- Chimenti, Franco,Fioravanti, Rossella,Bolasco, Adriana,Manna, Fedele,Chimenti, Paola,Secci, Daniela,Befani, Olivia,Turini, Paola,Ortuso, Francesco,Alcaro, Stefano
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p. 425 - 428
(2007/10/03)
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- Synthesis of some new 1-(6-fluorobenzothiazol-2-yl)-3-(4-fluoro- phenyl)-5-arylpyrazolines and their iodine(III) mediated oxidation to corresponding pyrazoles
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The reaction of fluorinated chalcones 2 and 6-fluorobenzothiazol-2- ylhydrazine 1 in presence of catalytic amount of glacial acetic acid in refluxing ethanol yields l-(6-fluorobenzothiazol-2-yl)-3-(4-fluorophenyl)-5- arylpyrazolines 3, which undergo facile oxidation to the corresponding pyrazoles 4 in good yield using iodobenzene diacetate (IBD). The structures of the synthesized compounds have been established on the basis of their elemental analysis, MS and 1H and 13C NMR spectroscopy.
- Aggarwal, Ranjana,Kumar, Vinod,Singh, Shiv P
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p. 1332 - 1336
(2008/09/18)
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- Biologically active 1,3-bis-aromatic-prop-2-en-1-ones, 1,3-bis-aromatic-propan-1-ones, and 1,3-bis-aromatic-prop-2-yn-1-ones
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The invention relates to the use of 1,3-bis-aromatic-prop-2-en-1-ones (chalcones), 1,3-bis-aromatic-propan-1-ones (dihydrochalcones), and 1,3-bis-aromatic-prop-2-yn-1-ones for the preparation of pharmaceutical compositions for the treatment or prophylaxis of a number of serious diseases including i) conditions relating to harmful effects of inflammatory cytokines, ii) conditions involving infection by Helicobacter species, iii) conditions involving infection by viruses, iv) neoplastic disorders, and v) conditions caused by microorganisms or parasites. The invention also relates to novel chalcones and dihydrochalcones (especially alkoxy substituted variants) having advantageous substitution patterns with respect to their effect as drug substances, and to methods of preparing them, as well as to pharmaceutical compositions comprising the novel chalcones. Moreover, the present invention relates to a method for the isolation of Leishmania fumarate reductase, QSAR methodologies for selecting potent compounds for the above-mentioned purposes.
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- Antileishmaniai chalcones: Statistical design, synthesis, and three- dimensional quantitative structure-activity relationship analysis
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A large number of substituted chalcones have been synthesized and tested for antileishmanial and lymphocyte-suppressing activities. A subset of the chalcones was designed by using statistical methods. 3D-QSAR analyses using 67 (antileishmanial activity) and 63 (lymphocyte-suppressing activity) of the compounds for the training sets and 9 compounds as an external validation set were performed by using the GRID/GOLPE methodology. The Smart Region Definition procedure with subsequent region selection as implemented in GOLPE reduced the number of variables to approximately 1300 yielding 3D-QSAR models of high quality (lymphocyte-suppressing model, R2 = 0.90, Q2 = 0.80; antileishmanial model, R2 = 0.73, Q2 = 0.63). The coefficient plots indicate that steric interactions between the chalcones and the target are of major importance for the potencies of the compounds. A comparison of the coefficient plots for the antileishmanial effect and the lymphocyte- suppressing activity discloses significant differences which should make it possible to design chalcones having a high antileishmanial activity without suppressing the proliferation of lymphocytes.
- Nielsen, Simon Feldb?k,Christensen, S?ren Br?gger,Cruciani, Gabriele,Kharazmi, Arsalan,Liljefors, Tommy
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p. 4819 - 4832
(2007/10/03)
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- Synthesis of 1,5-benzothiazepines: Part XVIII - Syntheses of potential, fluorinated 2,4-diaryl-8-ethoxy/fluoro-2,5-dihydro-1,5-benzothiazepines as prospective cardiovascular agents
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5-Ethoxy- and 5-fluoro-2-aminobenzenethiols have been reacted with fluorinated benzalacetophenones 2a-e to obtain respective 2,4-fluorinated diaryl-8-ethoxy/fluoro-2,5-dihydro-1,5-benzothiazepines (3a-j) in satisfactory yields (40-58 percent). These compo
- Upreti, Mani,Pant, Seema,Dandia, A.,Pant, Umesh C.
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p. 1181 - 1184
(2007/10/03)
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