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Structure-based design of a new class of highly selective aminoimidazo[1,2-a]pyridine-based inhibitors of cyclin dependent kinases.

Hamdouchi C, Zhong B, Mendoza J, Collins E, Jaramillo C, De Diego JE, Robertson D, Spencer CD, Anderson BD, Watkins SA, Zhang F, Brooks HB
Bioorg Med Chem Lett 15 1943-7 (2005)
Cited: 22 times
EuropePMC logo PMID: 15780638

Abstract

Structure-based design approach was successfully used to guide the evolution of imidazopyridine scaffold yielding new structural class of highly selective inhibitors of cyclin dependent kinases that were able to form a new interaction with an identified residue of the protein, Lys89. Compounds from this series have shown no detectable effect when tested against a representative set of other serine/threonine kinases such as GSK3beta, CAMKII, PKA, PKC-alpha,beta,epsilon,gamma. Compound 2i inhibits proliferation in HCT 116 cells in tissue culture. Synthesis, co-crystal structure of CDK2 in complex with compound 2i, and preliminary SAR study are disclosed.

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  3. Structure-based predictions of activity cliffs. Husby J, Bottegoni G, Kufareva I, Abagyan R, Cavalli A. J Chem Inf Model 55 1062-1076 (2015)
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Reviews citing this publication (2)

  1. Selectivity and potency of cyclin-dependent kinase inhibitors. Sridhar J, Akula N, Pattabiraman N. AAPS J 8 E204-21 (2006)
  2. Synthesis of Imidazo[1,2-a]pyridines: C-H Functionalization in the Direction of C-S Bond Formation. Ravi C, Adimurthy S. Chem Rec 17 1019-1038 (2017)

Articles citing this publication (15)

  1. Design, synthesis and in vitro antimicrobial evaluation of novel Imidazo[1,2-a]pyridine and imidazo[2,1-b][1,3]benzothiazole motifs. Al-Tel TH, Al-Qawasmeh RA, Zaarour R. Eur J Med Chem 46 1874-1881 (2011)
  2. Rhodium(II) acetate-catalyzed stereoselective synthesis, SAR and anti-HIV activity of novel oxindoles bearing cyclopropane ring. Kumari G, Nutan, Modi M, Gupta SK, Singh RK. Eur J Med Chem 46 1181-1188 (2011)
  3. Design and biological evaluation of imidazo[1,2-a]pyridines as novel and potent ASK1 inhibitors. Terao Y, Suzuki H, Yoshikawa M, Yashiro H, Takekawa S, Fujitani Y, Okada K, Inoue Y, Yamamoto Y, Nakagawa H, Yao S, Kawamoto T, Uchikawa O. Bioorg Med Chem Lett 22 7326-7329 (2012)
  4. Structure-based design of a novel class of potent inhibitors of InhA, the enoyl acyl carrier protein reductase from Mycobacterium tuberculosis: a computer modelling approach. Subba Rao G, Vijayakrishnan R, Kumar M. Chem Biol Drug Des 72 444-449 (2008)
  5. In silico structure-based design of a novel class of potent and selective small peptide inhibitor of Mycobacterium tuberculosis Dihydrofolate reductase, a potential target for anti-TB drug discovery. Kumar M, Vijayakrishnan R, Subba Rao G. Mol Divers 14 595-604 (2010)
  6. Structure-based design and synthesis of imidazo[1,2-a]pyridine derivatives as novel and potent Nek2 inhibitors with in vitro and in vivo antitumor activities. Xi JB, Fang YF, Frett B, Zhu ML, Zhu T, Kong YN, Guan FJ, Zhao Y, Zhang XW, Li HY, Ma ML, Hu W. Eur J Med Chem 126 1083-1106 (2017)
  7. Synthesis and biological evaluation of inhibitors of thymidine monophosphate kinase from Bacillus anthracis. Byun Y, Vogel SR, Phipps AJ, Carnrot C, Eriksson S, Tiwari R, Tjarks W. Nucleosides Nucleotides Nucleic Acids 27 244-260 (2008)
  8. A facile I2-catalyzed synthesis of imidazo[1,2-a]pyridines via sp3 C-H functionalization of azaarenes and evaluation of anticancer activity. Mani GS, Shaik SP, Tangella Y, Bale S, Godugu C, Kamal A. Org Biomol Chem 15 6780-6791 (2017)
  9. Structure-based design of 2-arylamino-4-cyclohexylmethoxy-5-nitroso-6-aminopyrimidine inhibitors of cyclin-dependent kinase 2. Marchetti F, Sayle KL, Bentley J, Clegg W, Curtin NJ, Endicott JA, Golding BT, Griffin RJ, Haggerty K, Harrington RW, Mesguiche V, Newell DR, Noble ME, Parsons RJ, Pratt DJ, Wang LZ, Hardcastle IR. Org Biomol Chem 5 1577-1585 (2007)
  10. Alumina-Supported Gold Nanoparticles as a Bifunctional Catalyst for the Synthesis of 2-Amino-3-arylimidazo[1,2-a]pyridines. Tzani MA, Kallitsakis MG, Symeonidis TS, Lykakis IN. ACS Omega 3 17947-17956 (2018)
  11. Molecular modeling, synthesis and biological evaluation of N-heteroaryl compounds as reverse transcriptase inhibitors against HIV-1. Singh A, Yadav D, Yadav M, Dhamanage A, Kulkarni S, Singh RK. Chem Biol Drug Des 85 336-347 (2015)
  12. Synthesis of Novel Imidazo[1,2-a]pyridin-2-amines from Arylamines and Nitriles via Sequential Addition and I2 /KI-Mediated Oxidative Cyclization. Tian X, Song L, Wang M, Lv Z, Wu J, Yu W, Chang J. Chemistry 22 7617-7622 (2016)
  13. Molecular Modeling, Synthesis, and Anti-HIV Activity of Novel Isoindolinedione Analogues as Potent Non-nucleoside Reverse Transcriptase Inhibitors. Kumari G, Singh RK. Chem Biol Drug Des 87 200-212 (2016)
  14. Molecular dynamics and QM/MM-based 3D interaction analyses of cyclin-E inhibitors. Pasha FA, Neaz MM. J Mol Model 19 879-891 (2013)
  15. Selective, C-3 Friedel-Crafts acylation to generate functionally diverse, acetylated Imidazo[1,2-a]pyridine derivatives. Frett B, McConnell N, Kharbanda A, Naresh G, Rounseville B, Warner C, Chang J, Debolske N, Li HY. Tetrahedron 74 4592-4600 (2018)


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