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1987 1
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Page 1
One-step protecting-group-free synthesis of azepinomycin in water.
Coggins AJ, Tocher DA, Powner MW. Coggins AJ, et al. Org Biomol Chem. 2015 Mar 21;13(11):3378-81. doi: 10.1039/c5ob00210a. Org Biomol Chem. 2015. PMID: 25658692 Free article.
We report an efficient, atom economical general acid-base catalyzed one-step multi-gram synthesis of azepinomycin from commercially available compounds in water. We propose that the described pH-dependent Amadori rearrangement, which couples an amino-imidazole and simple s …
We report an efficient, atom economical general acid-base catalyzed one-step multi-gram synthesis of azepinomycin from commercially a …
Synthesis of azepinomycin and its beta-D-ribofuranoside.
Isshiki K, Takahashi Y, Iinuma H, Naganawa H, Umezawa Y, Takeuchi T, Umezawa H, Nishimura S, Okada N, Tatsuta K. Isshiki K, et al. J Antibiot (Tokyo). 1987 Oct;40(10):1461-3. doi: 10.7164/antibiotics.40.1461. J Antibiot (Tokyo). 1987. PMID: 3680014 Free article. No abstract available.
Analogs of iso-azepinomycin as potential transition-state analog inhibitors of guanase: synthesis, biochemical screening, and structure-activity correlations of various selectively substituted imidazo[4,5-e][1,4]diazepines.
Tantravedi S, Chakraborty S, Shah NH, Fishbein JC, Hosmane RS. Tantravedi S, et al. Bioorg Med Chem. 2013 Sep 1;21(17):4893-903. doi: 10.1016/j.bmc.2013.06.069. Epub 2013 Jul 11. Bioorg Med Chem. 2013. PMID: 23891230 Free PMC article.
The work described herein is based on a hypothesis that azepinomycin, a heterocyclic natural product and a purported transition state analog inhibitor of guanase, does not represent the true transition state of the enzyme-catalyzed reaction as closely as does iso-azepin …
The work described herein is based on a hypothesis that azepinomycin, a heterocyclic natural product and a purported transition state …
A novel transition state analog inhibitor of guanase based on azepinomycin ring structure: Synthesis and biochemical assessment of enzyme inhibition.
Chakraborty S, Shah NH, Fishbein JC, Hosmane RS. Chakraborty S, et al. Bioorg Med Chem Lett. 2011 Jan 15;21(2):756-9. doi: 10.1016/j.bmcl.2010.11.109. Epub 2010 Nov 27. Bioorg Med Chem Lett. 2011. PMID: 21183343 Free PMC article.
Synthesis and biochemical inhibition studies of a novel transition state analog inhibitor of guanase bearing the ring structure of azepinomycin have been reported. The compound was synthesized in five-steps from a known compound and biochemically screened against the rabbi …
Synthesis and biochemical inhibition studies of a novel transition state analog inhibitor of guanase bearing the ring structure of azepin …
Investigations into specificity of azepinomycin for inhibition of guanase: discrimination between the natural heterocyclic inhibitor and its synthetic nucleoside analogues.
Chakraborty S, Shah NH, Fishbein JC, Hosmane RS. Chakraborty S, et al. Bioorg Med Chem Lett. 2012 Dec 1;22(23):7214-8. doi: 10.1016/j.bmcl.2012.09.053. Epub 2012 Oct 2. Bioorg Med Chem Lett. 2012. PMID: 23084905 Free PMC article.
In our long and broad program to explore structure-activity relationships of the natural product azepinomycin and its analogues for inhibition of guanase, an important enzyme of purine salvage pathway of nucleic acid metabolism, it became necessary to investigate if the nu …
In our long and broad program to explore structure-activity relationships of the natural product azepinomycin and its analogues for i …
Ring-expanded ("Fat") nucleosides as broad-spectrum anticancer and antiviral agents.
Hosmane RS. Hosmane RS. Curr Top Med Chem. 2002 Oct;2(10):1093-109. doi: 10.2174/1568026023393147. Curr Top Med Chem. 2002. PMID: 12173969 Review.
The important natural RENs include coformycin, pentostatin, azepinomycin, adechlorin, and adecypenol. A majority of them are synergistic antitumor and/or antiviral antibiotics which potentiate the effects of other antitumor or antiviral compounds through inhibition of key …
The important natural RENs include coformycin, pentostatin, azepinomycin, adechlorin, and adecypenol. A majority of them are synergis …
Investigations into biochemical mode of inhibition of guanase by azepinomycin: synthesis and biochemical screening of several analogues of azepinomycin.
Rajappan VP, Hosmane RS. Rajappan VP, et al. Nucleosides Nucleotides. 1999 Apr-May;18(4-5):835-6. doi: 10.1080/15257779908041573. Nucleosides Nucleotides. 1999. PMID: 10432688
In an effort to biochemical mode of guanase inhibition as well as the structure-activity relationships of azepinomycin, five analogues (I-V) of azepinomycin were synthesized and screened against guanase from rabbit liver. Our results suggest that while the 6-hydroxy …
In an effort to biochemical mode of guanase inhibition as well as the structure-activity relationships of azepinomycin, five analogue …
Purines. LXIII. Syntheses of azepinomycin, an antitumor antibiotic from Streptomyces species, and its 3-beta-D-ribofuranoside and their 8-imino analogues.
Fujii T, Saito T, Fujisawa T. Fujii T, et al. Chem Pharm Bull (Tokyo). 1994 Jun;42(6):1231-7. doi: 10.1248/cpb.42.1231. Chem Pharm Bull (Tokyo). 1994. PMID: 8069974 Free article.
Three variants of a synthetic route to the antitumor antibiotic azepinomycin (3) from 1-substituted N'-alkoxy-5-formamidoimidazole-4-carboxamidine (type 10) are described. ...
Three variants of a synthetic route to the antitumor antibiotic azepinomycin (3) from 1-substituted N'-alkoxy-5-formamidoimidazole-4- …
Analogues of azepinomycin as inhibitors of guanase.
Rajappan VP, Hosmane RS. Rajappan VP, et al. Nucleosides Nucleotides. 1998 Jul;17(7):1141-51. doi: 10.1080/07328319808004227. Nucleosides Nucleotides. 1998. PMID: 9708314
Synthesis and biochemical screening against guanase of analogues of the naturally occurring guanase inhibitor azepinomycin (2) are reported. Compound 6-amino-5,6,7,8,-tetrahydro-4H-imidazo[4,5-e][1,4]diazepine-5,8-dione (3) was synthesized in six steps commencing with 1-be …
Synthesis and biochemical screening against guanase of analogues of the naturally occurring guanase inhibitor azepinomycin (2) are re …
Design of inhibitors against guanase: synthesis and biochemical evaluation of analogues of azepinomycin.
Ujjinamatada RK, Bhan A, Hosmane RS. Ujjinamatada RK, et al. Bioorg Med Chem Lett. 2006 Nov 1;16(21):5551-4. doi: 10.1016/j.bmcl.2006.08.033. Epub 2006 Aug 22. Bioorg Med Chem Lett. 2006. PMID: 16920357
As part of a program to design rational, mechanism-based inhibitors of guanase, we report here the synthesis and biochemical screening of two analogues of azepinomycin (1 and 2), a naturally occurring inhibitor of guanase, known to mimic the transition-state of the enzyme- …
As part of a program to design rational, mechanism-based inhibitors of guanase, we report here the synthesis and biochemical screening of tw …
11 results