116548-04-0Relevant articles and documents
Synthesis of novel pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine derivatives and their cytotoxic activity
Naresh Kumar,Malla Reddy,Nagendar,Kurumurthy,Shanthan Rao,Karnewar, Santosh,Kotamraju, Srigiridhar,Narsaiah
, p. 1531 - 1535 (2015)
The 3-amino-6-(trifluoromethyl)furo[2,3-b]pyridine-2-carbohydrazide (5) was prepared from 3-cyano-6-trifluoromethyl-2(1H)pyridone (2) in series of steps via selective O-alkylation, Thorpe-Ziegler cyclization followed by reaction with hydrazine hydrate. The 2-carbohydrazide (5) was further reacted with aliphatic acids under different reaction temperatures to form a series of novel N-acylfuro[2,3-b]pyridine-2-carbohydrazide (6) and pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine derivatives (7). All the compounds 6 and 7 were screened for cytotoxic activity against breast carcinoma MD Anderson-Metastatic Breast (MDA-MB) 231 (aggressive) cell lines at 10 μM concentration. Compounds 6a, 6b, and 6c showed promising activity.
Synthesis of novel hydrazone and azole functionalized pyrazolo[3,4-b]pyridine derivatives as promising anticancer agents
Nagender,Naresh Kumar,Malla Reddy,Krishna Swaroop,Poornachandra,Ganesh Kumar,Narsaiah
, p. 4427 - 4432 (2016)
A series of novel pyrazolo[3,4-b]pyridine based target compounds were synthesized starting from the key intermediate ethyl 2-(3-amino-6-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl)acetate 5 on reaction with hydrazine hydrate followed by reaction with
Synthesis, cytotoxicity, antimicrobial and anti-biofilm activities of novel pyrazolo[3,4-b]pyridine and pyrimidine functionalized 1,2,3-triazole derivatives
Nagender,Malla Reddy,Naresh Kumar,Poornachandra,Ganesh Kumar,Narsaiah
, p. 2905 - 2908 (2014)
A series of novel pyrazolo[3,4-b]pyridine and pyrimidine functionalized 1,2,3-triazole derivatives 8a-g and 9a-g were prepared starting from 6-trifluoromethylpyridine-2(1H)one 2 via selective O-alkylation, followed by cyclisation using hydrazine hydrate to obtain 6-(trifluoromethyl)-1H-pyrazolo[3, 4-b]pyridin-3-amine 4. Compound 4 was diazotized followed by reaction with sodium azide, resulted in 3-azido-6-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine 5. Compound 5 was further cyclized with N-/O-propargylated pyrimidine derivatives under Sharpless conditions and obtained compounds 6 and 7, respectively. Each set of compounds 6 and 7 were alkylated with different alkyl halides and obtained respective products 8 and 9. All the products were screened for cytotoxicity against four human cancer cell lines such as A549-Lung (CCL-185), MCF7-Breast (HTB-22), DU145-Prostate (HTB-81) and HeLa-Cervical (CCL-2), compounds 9d, 9e and 9f which showed promising activity have been identified. The products were also screened for antimicrobial, anti bio-film and MBC activities. Promising compounds in each case have been identified.
Discovery of cyanopyridine scaffold as novel indoleamine-2,3-dioxygenase 1 (IDO1) inhibitors through virtual screening and preliminary hit optimisation
Xu, Xi,Ren, Jie,Ma, Yinghe,Liu, Hongting,Rong, Quanjin,Feng, Yifan,Wang, Yameng,Cheng, Yu,Ge, Ruijia,Li, Zhiyu,Bian, Jinlei
, p. 250 - 263 (2019)
With the aim of discovering novel IDO1 inhibitors, a combined similarity search and molecular docking approach was employed to the discovery of 32 hit compounds. Testing the screened hit compounds has led to several novel submicromolar inhibitors. Especially for compounds LVS-019 with cyanopyridine scaffold, showed good IDO1 inhibitory activity. To discover more compounds with similar structures to LVS-019, a shape-based model was then generated on the basis of it and the second-round virtual screening was carried out leading to 23 derivatives. Molecular docking studies suggested a possible binding mode of LVS-019, which provides a good starting point for the development of cyanopyridine scaffold compounds as potent IDO1 inhibitor. To improve potency of these hits, we further designed and synthesised another 14 derivatives of LVS-019. Among these compounds, LBJ-10 showed improved potency compared to the hits and displayed comparable potency to the control GDC-0919 analogue. LBJ-10 can serve as ideal leads for further modifications as IDO1 inhibitors for cancer treatment.
2-(Halogenated Phenyl) acetamides and propanamides as potent TRPV1 antagonists
Ann, Jihyae,Bahrenberg, Gregor,Blumberg, Peter M.,Choi, Sun,Christoph, Thomas,Do, Nayeon,Frank-Foltyn, Robert,Ha, Heejin,Jeong, Jin Ju,Kang, Jin Mi,Kim, Changhoon,Kwon, Sun Ok,Lee, Jeewoo,Lee, Sunho,Lesch, Bernhard,Stockhausen, Hannelore,Vu, Thi Ngoc Lan,Yoon, Sanghee
, (2021/07/28)
A series consisting of 117 2-(halogenated phenyl) acetamide and propanamide analogs were investigated as TRPV1 antagonists. The structure–activity analysis targeting their three pharmacophoric regions indicated that halogenated phenyl A-region analogs exhibited a broad functional profile ranging from agonism to antagonism. Among the compounds, antagonists 28 and 92 exhibited potent antagonism toward capsaicin for hTRPV1 with Ki[CAP] = 2.6 and 6.9 nM, respectively. Further, antagonist 92 displayed promising analgesic activity in vivo in both phases of the formalin mouse pain model. A molecular modeling study of 92 indicated that the two fluoro groups in the A-region made hydrophobic interactions with the receptor.
Synthesis of novel triazole functionalized pyridine derivatives as potential antimicrobial and anti-biofilm agents
Kumar, R. Naresh,Mallareddy,Nagender,Rao, P. Sambasiva,Poornachandra,Ranjithreddy,Kumar, C. Ganesh,Narsaiah
, p. 1361 - 1375 (2017/04/28)
A series of novel 1-substituted (1H-1,2,3-triazole-4-yl) methoxy functionalized pyridine derivatives 5 and 6 have been prepared starting from 2(1//) pyridone 1 via selective O-propargylation followed by reaction with diverse substituted azides under Sharpless conditions. All the compounds 5 and 6 have been screened for antimicrobial activity, minimum bactericidal concentration and biofilm inhibition activity. Compounds 5d, 51 and 5s which showed promising activity specifically towards Staphylococcus aureus MTCC 96 and Staphylococcus aureus MLS-16 MTCC 2940 have been identified. Further, in silico docking studies have been carried out on the inhibition of dehydrosqualene synthase enzyme of S. aureus. This is a key enzyme in the biosynthesis of staphyloxanthin, a virulence factor for S. aureus. Further, on screening for antioxidant activity, the compounds 51,5q and 5n showed promising activity.
6,6-Fused heterocyclic ureas as highly potent TRPV1 antagonists
Sun, Wei,Kim, Hyo-Shin,Lee, Sunho,Jung, Aeran,Kim, Sung-Eun,Ann, Jihyae,Yoon, Suyoung,Choi, Sun,Lee, Jin Hee,Blumberg, Peter M.,Frank-Foltyn, Robert,Bahrenberg, Gregor,Schiene, Klaus,Stockhausen, Hannelore,Christoph, Thomas,Frormann, Sven,Lee, Jeewoo
, p. 803 - 806 (2015/02/19)
A series of N-[{2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)-pyridin-3-yl}methyl] N′-(6,6-fused heterocyclic) ureas have been investigated as hTRPV1 antagonists. Among them, compound 15 showed highly potent TRPV1 antagonism to capsaicin, with Ki(ant) = 0.2 nM, as well as antagonism to other activators, and it was efficacious in a pain model. A docking study of 15 with our hTRPV1 homology model indicates that there is crucial hydrogen bonding between the ring nitrogen and the receptor, contributing to its potency.
Substituted Methanesulfonamide Derivatives as Vanilloid Receptor Ligands
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Paragraph 0265; 0267, (2013/04/10)
The invention relates to substituted methanesulfonamide derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseas
SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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Page/Page column 39; 40, (2013/04/13)
The invention relates to substituted methanesulfonamide derivatives as vanilloid receptor ligands of formula (I), to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and
SUBSTITUTED HETEROCYCLIC AZA DERIVATIVES
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Page/Page column 89; 90, (2013/03/26)
The invention relates to heterocyclic aza derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
