CCR5 receptor antagonists: Discovery and SAR study of guanylhydrazone derivatives
High throughput screening (HTS) led to the identification of the guanylhydrazone of 2-(4-chlorobenzyloxy)-5-bromobenzaldehyde as a CCR5 receptor antagonist. Modifications of the guanylhydrazone resulted in the discovery of novel CCR5 antagonists. High throughput screening (HTS) led to the identifica...
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Published in | Bioorganic & medicinal chemistry letters Vol. 17; no. 1; pp. 231 - 234 |
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Main Authors | , , , , , , , , , |
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Elsevier Ltd
2007
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Abstract | High throughput screening (HTS) led to the identification of the guanylhydrazone of 2-(4-chlorobenzyloxy)-5-bromobenzaldehyde as a CCR5 receptor antagonist. Modifications of the guanylhydrazone resulted in the discovery of novel CCR5 antagonists.
High throughput screening (HTS) led to the identification of the guanylhydrazone of 2-(4-chlorobenzyloxy)-5-bromobenzaldehyde as a CCR5 receptor antagonist. Initial modifications of the guanylhydrazone series indicated that substitution of the benzyl group at the para-position was well tolerated. Substitution at the 5-position of the central phenyl ring was critical for potency. Replacement of the guanylhydrazone group led to the discovery of a novel series of CCR5 antagonists. |
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AbstractList | High throughput screening (HTS) led to the identification of the guanylhydrazone of 2-(4-chlorobenzyloxy)-5-bromobenzaldehyde as a CCR5 receptor antagonist. Initial modifications of the guanylhydrazone series indicated that substitution of the benzyl group at the para-position was well tolerated. Substitution at the 5-position of the central phenyl ring was critical for potency. Replacement of the guanylhydrazone group led to the discovery of a novel series of CCR5 antagonists. High throughput screening (HTS) led to the identification of the guanylhydrazone of 2-(4-chlorobenzyloxy)-5-bromobenzaldehyde as a CCR5 receptor antagonist. Modifications of the guanylhydrazone resulted in the discovery of novel CCR5 antagonists. High throughput screening (HTS) led to the identification of the guanylhydrazone of 2-(4-chlorobenzyloxy)-5-bromobenzaldehyde as a CCR5 receptor antagonist. Initial modifications of the guanylhydrazone series indicated that substitution of the benzyl group at the para-position was well tolerated. Substitution at the 5-position of the central phenyl ring was critical for potency. Replacement of the guanylhydrazone group led to the discovery of a novel series of CCR5 antagonists. |
Author | Davey, Dave Chou, Yuo-Ling Dunning, Laura Wei, Robert G. Arnaiz, Damian O. Ye, Bin Lu, Shou-Fu Onuffer, James Phillips, Gary Lee, Wheeseong |
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Cites_doi | 10.1021/jm0304515 10.1016/S0960-894X(02)00918-6 10.1021/jm031046g 10.1016/j.bmc.2003.10.019 10.1016/j.bmcl.2003.12.004 10.1358/dof.2005.030.05.902712 10.1016/j.bmcl.2004.04.078 10.1016/S0960-894X(02)01063-6 10.1038/nm1296-1293 10.2174/15680266106061319 10.1016/j.bmcl.2004.12.044 10.1016/j.bmcl.2003.12.005 10.1016/j.bmcl.2003.12.006 10.1016/j.bmcl.2005.02.030 10.1016/j.bmcl.2004.10.044 10.1016/j.bmc.2004.10.021 10.1016/j.bmc.2004.10.013 |
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References | Tagat, J.; McCombie,S.; Nazareno, D.; Steensma, R.; Labroli, M.; Baroudy, B.; Strizki, J.; Cox, K. Kesicki, E. A.; Odingo, J. O.; Oliver, A. R.; Orme, M. W.; Schweickart, V. L.; Epp, A.; Gary, P. W.; Fowler, K. W. Abstracts of Papers, 221st Györgydeák, Holzer, Mereiter (bib4) 1999 bib5 Rosenkilde, Schwartz (bib6) 2006; 6 March 23–27, 2003, American Chemical Society: Washington, DC, 2003; MEDI 15. D’Souza, Harden (bib1) 1996; 2 , April 1–5, 2001, American Chemical Society: Washington, DC, 2001; MEDI 109. Shah (10.1016/j.bmcl.2006.09.052_bib2_13) 2005; 15 D’Souza (10.1016/j.bmcl.2006.09.052_bib1) 1996; 2 Thoma (10.1016/j.bmcl.2006.09.052_bib2_14) 2004; 47 10.1016/j.bmcl.2006.09.052_bib3 Burrows (10.1016/j.bmcl.2006.09.052_bib2_16) 2005; 15 Shankaran (10.1016/j.bmcl.2006.09.052_bib2_6) 2004; 14 Györgydeák (10.1016/j.bmcl.2006.09.052_bib4) 1999 McComie (10.1016/j.bmcl.2006.09.052_bib2_8) 2003; 13 Kim (10.1016/j.bmcl.2006.09.052_bib2_15) 2005; 15 Rosenkilde (10.1016/j.bmcl.2006.09.052_bib6) 2006; 6 Seto (10.1016/j.bmcl.2006.09.052_bib2_11) 2005; 13 Shen (10.1016/j.bmcl.2006.09.052_bib2_4) 2004; 14 Ginesta (10.1016/j.bmcl.2006.09.052_bib2_7) 2005; 30 Shen (10.1016/j.bmcl.2006.09.052_bib2_3) 2004; 14 Shu (10.1016/j.bmcl.2006.09.052_bib2_5) 2004; 14 Imamura (10.1016/j.bmcl.2006.09.052_bib2_12) 2005; 13 10.1016/j.bmcl.2006.09.052_bib2_2 Song (10.1016/j.bmcl.2006.09.052_bib2_9) 2004; 12 Palani (10.1016/j.bmcl.2006.09.052_bib2_1) 2003; 13 Tagat (10.1016/j.bmcl.2006.09.052_bib2_10) 2004; 47 |
References_xml | – start-page: 899 year: 1999 ident: bib4 publication-title: Monatshefte fűr Chemie contributor: fullname: Mereiter – ident: bib5 – volume: 6 start-page: 1319 year: 2006 ident: bib6 publication-title: Curr. Trends Med. Chem. contributor: fullname: Schwartz – volume: 2 start-page: 1293 year: 1996 ident: bib1 publication-title: Nat. Med. contributor: fullname: Harden – volume: 47 start-page: 2405 year: 2004 ident: 10.1016/j.bmcl.2006.09.052_bib2_10 publication-title: J. Med. Chem. doi: 10.1021/jm0304515 contributor: fullname: Tagat – ident: 10.1016/j.bmcl.2006.09.052_bib2_2 – volume: 13 start-page: 567 year: 2003 ident: 10.1016/j.bmcl.2006.09.052_bib2_8 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/S0960-894X(02)00918-6 contributor: fullname: McComie – volume: 47 start-page: 1939 year: 2004 ident: 10.1016/j.bmcl.2006.09.052_bib2_14 publication-title: J. Med. Chem. doi: 10.1021/jm031046g contributor: fullname: Thoma – volume: 12 start-page: 489 year: 2004 ident: 10.1016/j.bmcl.2006.09.052_bib2_9 publication-title: Bioorg. Med. Chem. doi: 10.1016/j.bmc.2003.10.019 contributor: fullname: Song – volume: 14 start-page: 935 year: 2004 ident: 10.1016/j.bmcl.2006.09.052_bib2_3 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/j.bmcl.2003.12.004 contributor: fullname: Shen – volume: 30 start-page: 469 year: 2005 ident: 10.1016/j.bmcl.2006.09.052_bib2_7 publication-title: Drugs Future doi: 10.1358/dof.2005.030.05.902712 contributor: fullname: Ginesta – volume: 14 start-page: 3419 year: 2004 ident: 10.1016/j.bmcl.2006.09.052_bib2_6 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/j.bmcl.2004.04.078 contributor: fullname: Shankaran – volume: 13 start-page: 709 year: 2003 ident: 10.1016/j.bmcl.2006.09.052_bib2_1 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/S0960-894X(02)01063-6 contributor: fullname: Palani – ident: 10.1016/j.bmcl.2006.09.052_bib3 – volume: 2 start-page: 1293 year: 1996 ident: 10.1016/j.bmcl.2006.09.052_bib1 publication-title: Nat. Med. doi: 10.1038/nm1296-1293 contributor: fullname: D’Souza – volume: 6 start-page: 1319 year: 2006 ident: 10.1016/j.bmcl.2006.09.052_bib6 publication-title: Curr. Trends Med. Chem. doi: 10.2174/15680266106061319 contributor: fullname: Rosenkilde – volume: 15 start-page: 977 year: 2005 ident: 10.1016/j.bmcl.2006.09.052_bib2_13 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/j.bmcl.2004.12.044 contributor: fullname: Shah – volume: 14 start-page: 941 year: 2004 ident: 10.1016/j.bmcl.2006.09.052_bib2_4 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/j.bmcl.2003.12.005 contributor: fullname: Shen – start-page: 899 year: 1999 ident: 10.1016/j.bmcl.2006.09.052_bib4 publication-title: Monatshefte fűr Chemie contributor: fullname: Györgydeák – volume: 14 start-page: 947 year: 2004 ident: 10.1016/j.bmcl.2006.09.052_bib2_5 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/j.bmcl.2003.12.006 contributor: fullname: Shu – volume: 15 start-page: 2129 year: 2005 ident: 10.1016/j.bmcl.2006.09.052_bib2_15 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/j.bmcl.2005.02.030 contributor: fullname: Kim – volume: 15 start-page: 25 year: 2005 ident: 10.1016/j.bmcl.2006.09.052_bib2_16 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/j.bmcl.2004.10.044 contributor: fullname: Burrows – volume: 13 start-page: 363 year: 2005 ident: 10.1016/j.bmcl.2006.09.052_bib2_11 publication-title: Bioorg. Med. Chem. doi: 10.1016/j.bmc.2004.10.021 contributor: fullname: Seto – volume: 13 start-page: 397 year: 2005 ident: 10.1016/j.bmcl.2006.09.052_bib2_12 publication-title: Bioorg. Med. Chem. doi: 10.1016/j.bmc.2004.10.013 contributor: fullname: Imamura |
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SubjectTerms | Anti-HIV Agents - chemical synthesis Anti-HIV Agents - chemistry Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis Anti-Inflammatory Agents, Non-Steroidal - chemistry CCR5 CCR5 Receptor Antagonists Cells, Cultured Chemokine receptor antagonists Drug Evaluation, Preclinical Humans Inhibitory Concentration 50 Mitoguazone - analogs & derivatives Structure-Activity Relationship |
Title | CCR5 receptor antagonists: Discovery and SAR study of guanylhydrazone derivatives |
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