- Synthesis and antimitotic properties of ortho-substituted polymethoxydiarylazolopyrimidines
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Ortho-substituted polymethoxydiarylazolopyrimidines were synthesized using polymethoxysubstituted benzaldehydes and acetophenones as starting material. X-ray crystallography data clearly confirmed that the subsequent cyclization of 3-amino-1,2,4-triazole
- Chernyshova, Natalia B.,Tsyganov, Dmitry V.,Khrustalev, Victor N.,Raihstat, Mikhail M.,Konyushkin, Leonid D.,Semenov, Roman V.,Semenova, Marina N.,Semenov, Victor V.
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- [a]-Phenanthrene-fused BF2 azadipyrromethene (AzaBODIPY) dyes as bright near-infrared fluorophores
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A new substitution pattern of BF2 azadipyrromethene (azaBODIPY) dyes was obtained by phenanthrene fusion through a key palladium-catalyzed intramolecular C-H activation reaction. These [a]-phenanthrene-fused azaBODIPYs have a near planar struct
- Sheng, Wanle,Cui, Jiuen,Ruan, Zheng,Yan, Lifeng,Wu, Qinghua,Yu, Changjiang,Wei, Yun,Hao, Erhong,Jiao, Lijuan
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- The influence of methoxy and ethoxy groups on supramolecular arrangement of two methoxy-chalcones
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The structures of two methoxylated chalcones, namely (E)-1-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one and (E)-3-(4-ethoxyphenyl)-1-(4-methoxyphenyl) prop-2-en-1-one, reveal the effect of the inclusion of the methoxyl and ethoxyl substitue
- Custodio, Jean M. F.,Faria, Eduardo C. M.,Sallum, Lóide O.,Duarte, Vitor S.,Vaz, Wesley F.,De Aquino, Gilberto L. B.,Carvalho, Paulo S.,Napolitano, Hamilton B.
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Read Online
- Design, synthesis, biological evaluation of 3,5-diaryl-4,5-dihydro-1H-pyrazole carbaldehydes as non-purine xanthine oxidase inhibitors: Tracing the anticancer mechanism via xanthine oxidase inhibition
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Xanthine oxidase (XO) has been primarily targeted for the development of anti-hyperuriciemic /anti-gout agents as it catalyzes the conversion of xanthine and hypoxanthine into uric acid. XO overexpression in various cancer is very well correlated due to r
- Joshi, Gaurav,Sharma, Manisha,Kalra, Sourav,Gavande, Navnath S.,Singh, Sandeep,Kumar, Raj
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- A novel series of benzothiazepine derivatives as tubulin polymerization inhibitors with anti-tumor potency
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In this work, a series of diaryl benzo[b][1,4]thiazepine derivatives D1-D36 were synthesized and screened as tubulin polymerization inhibitors with anti-tumor potency. They were designed by introducing the seven-member ring benzothiazepine as the linker f
- Wang, Bin,Wang, Li-Ren,Liu, Lu-Lu,Wang, Wei,Man, Ruo-Jun,Zheng, Da-Jun,Deng, Yu-Shan,Yang, Yu-Shun,Xu, Chen,Zhu, Hai-Liang
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- Chalcones bearing a 3,4,5-trimethoxyphenyl motif are capable of selectively inhibiting oncogenic K-Ras signaling
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Ras proteins are small GTPases which regulate cellular proliferation, differentiation, and apoptosis. Constitutively active mutant Ras are expressed in ~15–20% human cancers, and K-Ras mutations account for ~85% of all Ras mutations. Despite the significa
- Cho, Kwang-jin,Fourman, Cody,Ketcha, Daniel M.,Kinstedt, Christine,Kovar, Sarah E.,Morris, Christopher,Williams, Brandon
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supporting information
(2020/04/15)
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- The synthesis of chalcones as anticancer prodrugs and their bioactivation in CYP1 expressing breast cancer cells
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Background: Although the expression levels of many P450s differ between tumour and corresponding normal tissue, CYP1B1 is one of the few CYP subfamilies which is significantly and consistently overexpressed in tumours. CYP1B1 has been shown to be active within tumours and is capable of metabolising a structurally diverse range of anticancer drugs. Because of this, and its role in the activation of procarcinogens, CYP1B1 is seen as an important target for anticancer drug development. Objective: To synthesise a series of chalcone derivatives based on the chemopreventative agent DMU-135 and investigate their antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1. Method: A series of chalcones were synthesised in yields of 43-94% using the Claisen-Schmidt condensation reaction. These were screened using a MTT assay against a panel of breast cancer cell lines which have been characterised for CYP1 expression. Result: A number of derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing significantly lower toxicity towards a non-tumour breast cell line with no CYP expression. Experiments using the CYP1 inhibitors acacetin and α-naphthoflavone provided supporting evidence for the involvement of CYP1 enzymes in the bioactivation of these compounds. Conclusion: Chalcones show promise as anticancer agents with evidence suggesting that CYP1 activation of these compounds may be involved.
- Ruparelia, Ketan C.,Zeka, Keti,Ijaz, Taeeba,Ankrett, Dyan N.,Wilsher, Nicola E.,Butler, Paul C.,Tan, Hoon L.,Lodhi, Sabahat,Bhambra, Avninder S.,Potter, Gerard A.,Arroo, Randolph R.J.,Beresford, Kenneth J.M.
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p. 322 - 332
(2018/06/26)
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- Synthesis and antimitotic properties of ortho-substituted polymethoxydiarylazolopyrimidines
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Ortho-substituted polymethoxydiarylazolopyrimidines were synthesized using polymethoxysubstituted benzaldehydes and acetophenones as starting material. X-ray crystallography data clearly confirmed that the subsequent cyclization of 3-amino-1,2,4-triazole
- Chernyshova, Natalia B.,Tsyganov, Dmitry V.,Khrustalev, Victor N.,Raihstat, Mikhail M.,Konyushkin, Leonid D.,Semenov, Roman V.,Semenova, Marina N.,Semenov, Victor V.
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p. 151 - 165
(2017/07/05)
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- Azine-Hydrazone Tautomerism of Guanylhydrazones: Evidence for the Preference Toward the Azine Tautomer
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Guanylhydrazones have been known for a long time and have wide applications in organic synthesis, medicinal chemistry, and material science; however, little attention has been paid toward their electronic and structural properties. Quantum chemical analysis on several therapeutically important guanylhydrazones indicated that all of them prefer the azine tautomeric state (by about 3-12 kcal/mol). A set of simple and conjugated azines were designed using quantum chemical methods, whose tautomeric preference toward the azine tautomer is in the range of 3-8 kcal/mol. Twenty new azines were synthesized and isolated in their neutral state. Variable temperature NMR study suggests existence of the azine tautomer even at higher temperatures with no traces of the hydrazone tautomer. The crystal structures of two representative compounds confirmed that the title compounds prefer to exist in their azine tautomeric form.
- Chourasiya, Sumit S.,Kathuria, Deepika,Nikam, Sampada S.,Ramakrishnan, Ashok,Khullar, Sadhika,Mandal, Sanjay K.,Chakraborti, Asit K.,Bharatam, Prasad V.
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p. 7574 - 7583
(2016/09/09)
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- Microwave-Assisted condensation reactions of acetophenone derivatives and activated methylene compounds with aldehydes catalyzed by boric acid under solvent-free conditions
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We here disclosed a new protocol for the condensation of acetophenone derivatives and active methylene compounds with aldehydes in the presence of boric acid under microwave conditions. Implementation of the reaction is simple, healthy and environmentally
- Brun, Elodie,Safer, Abdelmounaim,Carreaux, Franois,Bourahla, Khadidja,L'Helgoua'ch, Jean-Martial,Bazureau, Jean-Pierre,Villalgordo, Jose Manuel
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p. 11617 - 11631
(2015/08/06)
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- Synthesis and cytotoxic evaluation of alkoxylated chalcones
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A series of chalcones a1-20 bearing a 4-OMe groups on the A-ring were initially synthesized and their anticancer activities towards HepG2 cells evaluated. Subsequently, a series of chalcones b1-42 bearing methoxy groups at the 2′ and 6′-positions of the B-ring were synthesized and their anticancer activities towards five human cancer cell lines (HepG2, HeLa, MCF-7, A549 and SW1990) and two non-tumoral human cell lines evaluated. The results showed that six compounds (b6, b8, b11, b16, b18, b22, b23 and b29) displayed promising activities, with compounds b22 and b29 in particular showing higher levels of activity than etoposide against all five cancer cell lines. Compound b29 showed a promising SI value compared with both HMLE and L02 (2.1-6.5 fold in HMLE and > 33 > 103.1 fold in L02, respectively).
- Bai, Xiao-Guang,Xu, Chang-Liang,Zhao, Shuang-Shuang,He, Hong-Wei,Wang, Yu-Cheng,Wang, Ju-Xian
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p. 17256 - 17278
(2015/01/08)
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- Syntheses of 2-methoxyestradiol and eugenol template based diarylpropenes as non-steroidal anticancer agents
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Syntheses of 2-methoxyestradiol (1) and eugenol (6) template based conformationally flexible and rigid diarylpropenes, 14(a-l) and 20(a-e), as nonsteroidal anticancer agents have been performed. The synthesized compounds were evaluated for their anticance
- Pathak, Vinay,Ahmad, Imran,Kahlon, Amandeep Kaur,Hasanain, Mohammad,Sharma, Sandeep,Srivastava, Kishore K.,Sarkar, Jayanta,Shankar, Karuna,Sharma, Ashok,Gupta, Atul
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p. 35171 - 35185
(2014/11/07)
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- Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agents
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A series of substituted chalcones and their corresponding pyrazoles were synthesized and evaluated for in vitro cytotoxic activity against a panel of human cancer cell lines. Out of 93 compounds screened, 8 compounds, 1s, 3i,j,n, 4i,j,n and 4s, showed marked activity. Compounds 4j,n and 4s were found to be the most promising in this study. SAR is also discussed.
- Bhat,Dhar,Puri,Saxena,Shanmugavel,Qazi
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p. 3177 - 3180
(2007/10/03)
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- Structure-activity relationships in a series of orally active γ- hydroxy butenolide endothelin antagonists
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The design of potent and selective non-peptide antagonists of endothelin-1 (ET-1) and its related isopeptides are important tools defining the role of ET in human diseases. In this report we will describe the detailed structure-activity relationship (SAR) studies that led to the discovery of a potent series of butenolide ET(A) selective antagonists. Starting from a micromolar screening hit, PD012527, use of Topliss decision tree analysis led to the discovery of the nanomolar ET(A) selective antagonist PD155080. Further structural modifications around the butenolide ring led directly to the subnanomolar ET(A) selective antagonist PD156707, IC50's = 0.3 (ET(A)) and 780 nM (ET(B)). This series of compounds exhibited functional activity exemplified by PD156707. This derivative inhibited the ET(A) receptor mediated release of arachidonic acid from rabbit renal artery vascular smooth muscle cells with an IC50 = 1.1 nM and also inhibited the ET-1 induced contraction of rabbit femoral artery rings (ET(A) mediated) with a pA2 = 7.6. PD156707 also displayed in vivo functional activity inhibiting the hemodynamic responses due to exogenous administration of ET-1 in rats in a dose dependent fashion. Evidence for the pH dependence of the open and closed tautomerization forms of PD156707 was demonstrated by an NMR study. X- ray crystallographic analysis of the closed butenolide form of PD156707 shows the benzylic group located on the same side of the butenolide ring as the γ- hydroxyl and the remaining two phenyl groups on the butenolide ring essentially orthogonal to the butenolide ring. Pharmacokinetic parameters for PD156707 in dogs are also presented.
- Patt, William C.,Edmunds, Jeremy J.,Repine, Joseph T.,Berryman, Kent A.,Reisdorph, Billy R.,Lee, Chet,Plummer, Mark S.,Shahripour, Aurash,Haleen, Stephen J.,Keiser, Joan A.,Flynn, Mike A.,Welch, Kathleen M.,Reynolds, Elwood E.,Rubin, Ron,Tobias, Brian,Hallak, Hussein,Doherty, Annette M.
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p. 1063 - 1074
(2007/10/03)
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- Carbonic anhydrase inhibitors. Part 36*. Inhibition of isozymes I and II with Schiff bases derived from chalkones and aromatic/heterocyclic sulfonamides
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A series of 27 Schiff bases was prepared by reaction of chalkones with sulfanilamide and 5-amino-1,3,4-thiadiazole-2-sulfonamide. The new compounds were characterized by analysis and standard physico-chemical methods. They possess good inhibitory properties towards isozymes I and II of carbonic anhydrase. Structure-activity effects in this series of inhibitors are also discussed.
- Supuran,Popescu,Ilisiu,Costandache,Banciu
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p. 439 - 447
(2007/10/03)
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- Studies on Cycloimmonium Ylids: Synthesis of Some New 2,4,6-Triarylsubstituted Pyridines via Pyridinium Ylids
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2,4,6-Triarylsubstituted pyridines (4a-r) have been synthesised by the reaction of pyridinium ylids (1a-c) with α,β-unsaturated ketones (2a-f) in the presence of ammonium acetate and acetic acid.These compounds (4a-r) have been characterised on the basis
- Singhal, R. K.,Mishra, Naresh K.
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p. 1079 - 1080
(2007/10/02)
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