- Design and structure-activity relationships anticandidosic of diazaheteroaryl functionalized by Micha?l acceptors
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Benzimidazole and imidazopyridine heterocycles associated with Micha?l acceptors have shown strong anticandidosic potential in our previous work. After a decade of research, we have designed, synthesized and evaluated the anticandidosic activities of seve
- Aboudramane, Kone,Doumade, Zon,Drissa, Sissouma,Jean-Paul, N'Guessan D.,Mahama, Ouattara,Mamidou, Koné Witabouna,Songuigama, Coulibaly
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p. 117 - 133
(2022/02/14)
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- DERIVATIVES OF 4-(IMIDAZO[L,2-A]PYRIDIN-3-YL)-N-(PYRIDINYL)PYRIMIDIN- 2-AMINE AS THERAPEUTIC AGENTS
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A novel class of heteroaryl compounds for use in the prevention and/or treatment of proliferative diseases and conditions including cancers. The compounds are considered to be capable of inhibiting cell proliferation by inhibiting the activity of FLT3 and its mutant forms and/or other protein kinases such as CDKs. The compounds have the general structure I:
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Paragraph 0083; 00105
(2021/01/29)
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- PHARMACEUTICAL COMPOUNDS AND THERAPEUTIC METHODS
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The invention provides compounds of formula (16) and (17); and salts thereof, as well as compositions comprising such compounds and salts, complexes comprising such compounds and salts, and methods for treating cancer, inhibiting BMI1 expression, or treating Huntington's disease using such compounds, salts, and complexes. The compounds, salts, and complexes have potency, permeability, and oral bioavailability that make them particularly useful, for example, for the treatment of glioblastoma.
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Page/Page column 12-13
(2020/06/19)
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- Metal free coupling of heteroaryl N-tosylhydrazones and thiols: Efficient synthesis of sulfides
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A metal free coupling of heteroaromatic N-tosylhydrazones with thiols is presented. A convenient synthetic route to synthesize heteroaryl N-tosylhydrazones is also showed. Valuable thioethers with pyrroles, pyridines, thieno[2,3-b]pyridines, imidazo[1,2-a]pyridines, and 6H-thieno[2,3-b]pyrroles derivatives were synthesized in good yields. This coupling reaction can be carried out in a one-pot fashion and scaled up to the gram scale by using heteroaryl aldehydes, without the need to isolate the N-tosylhydrazone.
- García-Carrillo, Mario Alfredo,Guzmán, ángel,Díaz, Eduardo
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supporting information
p. 1952 - 1956
(2017/04/27)
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- NBS mediated protocol for the synthesis of N-bridged fused heterocycles in water
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A facile and environmental friendly protocol for the synthesis of N-bridged fused bicyclic compounds such as imidazo[1,2-a]pyridines, imidazo[1,2-a]pyrimidines, and imidazo[2,1-b]thiazole, from commercially available starting materials has been developed.
- Bhagat, Saket B.,Telvekar, Vikas N.
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supporting information
p. 3662 - 3666
(2017/08/23)
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- 2-Aminopyridines as an α-Bromination Shuttle in a Transition Metal-Free One-Pot Synthesis of Imidazo[1,2-a]pyridines
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A wide range of imidazo[1,2-a]pyridines are accessible from cheap and readily available 2-aminopyridines and 1,3-dicarbonyl compounds using a unique CBrCl3/2-aminopyridine system for bromination at the α-carbon. 2-Aminopyridine is not only the substrate but also acts as a bromination shuttle, transferring the bromine atom from CBrCl3 to the α-carbon of the 1,3-dicarbonyl. The reaction mechanism involves a series of reversible steps, including an addition reaction with cyclic transition state, to form a bromo-hemiaminal intermediate. Isolated yields of up to 97% were obtained under mild conditions and at short reaction times in this transition metal-free, one-pot synthesis.
- Roslan, Irwan Iskandar,Ng, Kian-Hong,Chuah, Gaik-Khuan,Jaenicke, Stephan
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supporting information
p. 364 - 369
(2016/04/26)
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- CBr4 Mediated Oxidative C-N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]pyridines and Imidazo[1,2-α]pyrimidines
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The carbon tetrabromide mediated oxidative carbon-nitrogen bond formation of 2-aminopyridines or 2-aminopyrimidines with β-keto esters or 1,3-diones, leading to a variety of complex imidazo[1,2-α]pyridines or imidazo[1,2-α]pyrimidines, is reported. The re
- Huo, Congde,Tang, Jing,Xie, Haisheng,Wang, Yajun,Dong, Jie
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supporting information
p. 1016 - 1019
(2016/03/15)
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- Double (amino-sulfur generation of formic acid ) - 1,3-propane diester compound and its synthetic method, pharmaceutical composition and use thereof
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The invention relates to a bis(aminodithioformate)-1,3-propane diester compound, and synthesis method thereof, a pharmaceutical composition containing the compound and a use, and especially relates to the use in preparing drugs for treating or preventing cancers. The compound is represented as the formula (I), wherein A is selected from substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic group, R1 and R2 are the same or different and are independently selected from hydrogen, alkyl, aryl alkyl or heteroaryl alkyl, or a substituted or unsubstituted heterocyclic ring formed together by the R1, the R2 and an N atom connected with the R1 and the R2.
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-
Paragraph 0320-0323
(2016/10/08)
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- Imidazopyridinyl-arylpropenone compounds as potential new anti-infective agents
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This paper describes the design by juxtaposition of anti-infectious moieties, a series of hybrid imidazopyridinyl-arylpropenone compounds. These compounds (5a-y) were synthesized by a crotonization reaction of 1-(2-methylimidazo[1,2-a]pyridin-3-yl)ethanone (3) with benzaldehyde derivatives (4). Spectral determination of structure of those compounds was performed by NMR and ESI mass spectroscopy. From the screening of antiparasitic and antimicrobial activities, the compound 5q (IC50 Combining double low line 1.52 μM) was identified for possible development against a chloroquine-resistant strain of Plasmodium falciparum. The compounds 5n, 5s and 5w showed a veterinary interest due to their nematicidal activities (LC100) against Haemonchus contortus from 7.1 to 1.5 nM. Against candidiasis, three other compounds (5e, 5g, 5v) inhibited drug-resistant strains of Candida albicans (MIQ Combining double low line 1.25 to 0.31 μg). This study showed that the arylpropenone functional group vectorised by imidazopyridine could be considered as a new pharmacophore with potential anti-infectious activities.
- Ouattara, Mahama,Sissouma, Drissa,Koné, Mamidou W.,Yavo, William
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p. 850 - 856
(2016/07/06)
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- Discovery and optimization of novel dual dithiocarbamates as potent anticancer agents
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A series of dual dithiocarbamates were synthesized and evaluated for their in-vitro anticancer activities on human non-small cell lung cancer cell line H460. Nine compounds exhibited significant antiproliferative activities with IC50 less than 1 μM. Among them, compound 14m showed the highest inhibitory activity against H460 cell and inhibited the growth of nine types of tumor cells with IC50 values less than 1 μM. It also achieved IC50 of 54 nM and 23 nM against HepG2 and MCF-7 cell lines, respectively. Preliminary structure-activity relationship study indicated that: a) when the methyl group (region A) is substituted with benzene rings, ortho substitution on the benzene ring is favored for activity; b) substitution with heterocyclic structures at region A exhibited greater impact on the anti-tumor activity of compounds, in which pyridine ring, thiazole ring, coumarin and benzo[b]thiophene are favored and quinoline ring is the most favored; c) substitution with different amines (region B) also showed marked effect on the activity of compounds and dimethylamine and morpholine are preferred to other tested amines.
- Li, Ri-Dong,Wang, Hui-Ling,Li, Ying-Bo,Wang, Zhong-Qing,Wang, Xin,Wang, Yi-Tao,Ge, Ze-Mei,Li, Run-Tao
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p. 381 - 391
(2015/03/04)
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- Inhibiting NF-κB-inducing kinase (NIK): Discovery, structure-based design, synthesis, structure-activity relationship, and co-crystal structures
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The discovery, structure-based design, synthesis, and optimization of NIK inhibitors are described. Our work began with an HTS hit, imidazopyridinyl pyrimidinamine 1. We utilized homology modeling and conformational analysis to optimize the indole scaffol
- Li, Kexue,McGee, Lawrence R.,Fisher, Ben,Sudom, Athena,Liu, Jinsong,Rubenstein, Steven M.,Anwer, Mohmed K.,Cushing, Timothy D.,Shin, Youngsook,Ayres, Merrill,Lee, Fei,Eksterowicz, John,Faulder, Paul,Waszkowycz, Bohdan,Plotnikova, Olga,Farrelly, Ellyn,Xiao, Shou-Hua,Chen, Guoqing,Wang, Zhulun
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p. 1238 - 1244
(2013/03/28)
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- Synthesis of imidazo[1,2-a]pyridines by the bis(acetyloxy)(phenyl)- λ3-iodane-Mediated oxidative coupling of 2-aminopyridines with β-keto esters and 1,3-diones
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Imidazo[1,2-a]pyridine-3-carboxylates can be prepared directly from 2-aminopyridines and β-keto esters by using bis(acetyloxy)(phenyl)- λ3-iodane as an oxidant and boron trifluoride etherate as a catalyst. The amount of catalyst plays a key rol
- Wang, Xianpei,Ma, Lijuan,Yu, Wei
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supporting information; experimental part
p. 2445 - 2453
(2011/09/15)
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- TBAI-catalyzed oxidative coupling of aminopyridines with β-keto esters and 1,3-diones - Synthesis of imidazo[1,2-a]pyridines
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TBAI could catalyze the direct oxidative C-N coupling of 2-aminopyridines with β-keto esters and 1,3-diones, which affords imidazo[1,2-a]pyridines as the products. The reaction was realized under metal-free conditions by using tert-butyl hydroperoxide (TB
- Ma, Lijuan,Wang, Xianpei,Yu, Wei,Han, Bing
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supporting information; experimental part
p. 11333 - 11335
(2011/11/29)
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- Synthesis, characterization and antibacterial evaluation of few 2, 3-substituted quinoxalines
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The quinoxaline derivatives (i-v) were synthesized through cyclization-oxidation of α- bromo carbonyl compounds with o-phenyl diamines (7a and 10a) and further coupling at 6-position via Suzuki reaction using PdCl2 (dppf).DCM, ter. BuNH2, Na2CO 3 in IPA, H2O refluxed for 16 h. As the results of antibacterial screening tests done by paper disc method, quinoxaline derivatives (i) and (v) revealed significant inhibition zone on Bacillus spericus and quinoxaline derivatives (iii) and (v) on Escherichia coli cultures.
- Reddy, B. Jayachandra,Reddy, M.C. Somasekhara
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experimental part
p. 483 - 485
(2011/12/02)
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- FUSED HETEROCYCLYC INHIBITOR COMPOUNDS
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The present invention provides a compound of general Formula (I) having histone deacetylase (HDAC) and/or Cyclin-dependent kinase (CDK) inhibitory activity, a pharmaceutical composition comprising the compound, and a method useful to treat diseases using the compound
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Page/Page column 61
(2010/03/02)
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- IMIDAZOPYRIDINYL THIAZOLYL HISTONE DEACETYLASE INHIBITORS
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A compound of general Formula (I) having histone deacetylase (HDAC) and/or CDK inhibitory activity, a pharmaceutical composition comprising the compound, and a method useful to treat diseases using the compound.
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Page/Page column 140
(2009/01/24)
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- NOVEL SUBSTITUTED IMIDAZOLE DERIVATIVES
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The present invention relates to a compound represented by Formula [I] or a pharmaceutically acceptable salt or ester thereof: wherein: X1, X2, X3, and X4, which may be identical or different, are each C or N, provided that none to two of X1, X2, X3, and X4 is/are N; Y is CH or N; R1, R1', R2, R2', R3, R3', R4, and R4', which may be identical or different, are each a hydrogen atom, a lower alkyl group, or the like; R5 is a hydrogen atom or a methyl group; R6 and R7, which may be identical or different, are each a hydrogen atom, a lower alkyl group, or the like; R8 and R8', which may be identical or different, are each a hydrogen atom, a lower alkyl group, or the like; R9 is an aryl group or a heteroaryl group which may be substituted; and n is an integer from 1 to 3, and a PLK1 inhibitor or an anticancer agent containing the same.
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Page/Page column 56
(2010/11/27)
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- INHIBITORS OF HISTONE DEACETYLASE
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The invention relates to a series of compounds useful for inhibiting histone deacetylase (HDAC) enzymatic activity. The invention also provides a method for inhibiting histone descetylase in a cell using said compounds as well as a method for treating cell proliferative diseases and conditions using said HDAC inhibitors. Further, the invention provides pharmaceutical compositions comprising the HDAC inhibiting compounds and a pharmaceutically acceptable carrier.
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Page/Page column 178-179
(2010/02/14)
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- Imidazo[1,2-a]pyridines. Part 2: SAR and optimisation of a potent and selective class of cyclin-dependent kinase inhibitors
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Exploration of SAR and optimisation of the imidazo[1,2-a]pyridine CDK inhibitors has lead to the discovery of novel, potent and selective inhibitors of the cyclin-dependent kinase CDK2. Understanding of SAR has identified positions of substitution, which allow modification of physical properties and offer the potential for in vivo optimisation.
- Byth, Kate F.,Culshaw, Janet D.,Green, Stephen,Oakes, Sandra E.,Thomas, Andrew P.
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p. 2245 - 2248
(2007/10/03)
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- Imidazo[1,2-a]pyridines: A potent and selective class of cyclin-dependent kinase inhibitors identified through structure-based hybridisation
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High-throughput screening identified the imidazo[1,2-a]pyridine and bisanilinopyrimidine series as inhibitors of the cyclin-dependent kinase CDK4. Comparison of their experimentally-determined binding modes and emerging structure-activity trends led to th
- Anderson, Malcolm,Beattie, John F.,Breault, Gloria A.,Breed, Jason,Byth, Kate F.,Culshaw, Janet D.,Ellston, Rebecca P. A.,Green, Stephen,Minshull, Claire A.,Norman, Richard A.,Pauptit, Richard A.,Stanway, Judith,Thomas, Andrew P.,Jewsbury, Philip J.
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p. 3021 - 3026
(2007/10/03)
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- IMIDAZO[1,2-A]PYRIDINE AND PYRAZOLO[2,3-A]PYRIDINE DERIVATIVES
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A compound of formula (I) wherein Ring A is imidazol[1,2a]pyrid-3-yl or pyrazolo[2,3a]pyrid-3-yl; Ris as defined within; m is 0-5; wherein the values of Rmay be the same or different; Ris as defined within; n is 0 to 2, wherein the values of Rmay be the same or different; Ring B is phenyl or phenyl fused to a C5-7cycloalkyl ring; Ris as defined within; p is 0-4; wherein the values of Rmay be the same or different; Ris as defined within; q is 0-2; wherein the values of Rmay be the same or different; and wherein p+q=5; or a pharmaceutically acceptable salt or an in vivo hydrolyzable ester thereof is described. The use of compounds of formula (I) in the inhibition of cell cycle kinases CDK2, CDK4, and CDK6 are also described. Pharmaceutical compositions, methods and processes for preparation of compounds of formula (I) are detailed.
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Page/Page column 33
(2010/02/04)
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- Synthesis and biological activity of 3-substituted imidazo[1,2-a]pyridines as antiulcer agents
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New imidazo[1,2-a]pyridines substituted at the 3-position have been synthesized as potential antisecretory and cytoprotective antiulcer agents. The synthetic routes began with cyclization of aminopyridines 5a,b and chloro ketones 6a,b to give imidazo[1,2-
- Starrett Jr.,Montzka,Crosswell,Cavanagh
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p. 2204 - 2210
(2007/10/02)
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