2-(2-acetylthiazol-4-yl)-4-thiazolecarboxylic acid | 21313-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-acetylthiazol-4-yl)-4-thiazolecarboxylic acid
• 英文别名: saramycetic acid I；saramycetic acid；2'-Acetyl-[2,4'-bithiazole]-4-carboxylic acid；2-(2-acetyl-1,3-thiazol-4-yl)-1,3-thiazole-4-carboxylic acid
• CAS: 21313-30-4
• 化学式: C₉H₆N₂O₃S₂
• 分子量: 254.29
• InChiKey: OGPKLDBXYIZETD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-(2-acetylthiazol-4-yl)-4-thiazolecarboxylic acid 在 盐酸 作用下， 反应 6.0h， 以70%的产率得到methyl saramycetate
  参考文献：
  名称：

  An RNA polymerase inhibitor, cyclothiazomycin B1, and its isomer

  摘要：

  Novel cyclic thiopeptides, cyclothiazomycins B1 (1) and B2 (2), were isolated from Streptomyces sp. A307 as potent hyphal swelling inducing substances. They are stable in the solid state but slowly isomerize with one another in solution. Degradation experiments and spectroscopic analyses disclosed that they comprise unique tricyclic structures each containing a dehydroalanine, and two dehydrohomoalanine residues, along with three thiazolines, three thiazoles, and a trisubstituted pyridine. Cyclothiazomycin B1 (1) is expected to be a powerful tool for DNA-RNA transcription studies, because this cyclopeptide inhibits DNA-dependent RNA synthesis by bacteriophage RNA polymerases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.006
• 作为产物：
  描述：

  ethyl saramycetate 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以100%的产率得到2-(2-acetylthiazol-4-yl)-4-thiazolecarboxylic acid
  参考文献：
  名称：

  Synthesis of saramycetic acid

  摘要：

  The first reported synthesis of saramycetic acid, a degradation product of the complex thiopeptide antibiotic cyclothiazomycin, is achieved in nine steps and 11% overall yield from diethoxyacetonitrile by a strategy, which incorporates two Hantzsch thiazole syntheses using thioamides prepared from the corresponding nitriles without the use of gaseous H2S. The synthetic material was transformed to methyl saramycetate, which had spectroscopic Properties in excellent agreement with the literature data. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.111

文献信息

• Structure of cyclothiazomycin, a unique polythiazole-containing peptide with renin inhibitory activity. Part 1. Chemistry and partial structures of cyclothiazomycin
  作者：Masahiro Aoki、Tatsuo Ohtsuka、Yoshiko Itezono、Kazuteru Yokose、Kazuo Furihata、Haruo Seto

  DOI：10.1016/0040-4039(91)80859-5

  日期：1991.1

  Cyclothiazomycin is a novel renin inhibitor produced by .NR0516 (IC50 1.66μM). Its molecular formula was determined to be C59H64H18O14S7 (MW .1472) based on high-resolution FAB mass and NMR spectroscopy. Five fragments of cyclothiazomycin containing thiazole, thiazoline, heterocyclic chromophore were clarified by extensive 2D-NMR experiments.

  Cyclothiazomycin是通过产生一个新的肾素抑制剂.NR0516（IC 50 1.66μM）。根据高分辨率FAB质谱和NMR光谱确定其分子式为C 59 H 64 H 18 O 14 S 7（MW .1472）。通过广泛的2D-NMR实验澄清了含有噻唑，噻唑啉，杂环发色团的环噻唑霉素的五个片段。
• Highly Efficient Borylation Suzuki Coupling Process for 4-Bromo-2-ketothiazoles: Straightforward Access to Micrococcinate and Saramycetate Esters
  作者：Thibaut Martin、Claire Laguerre、Christophe Hoarau、Francis Marsais

  DOI：10.1021/ol901525t

  日期：2009.8.20

  The first palladium-catalyzed borylation of 4-bromo-2-ketothiazoles followed by a Suzuki cross-coupling reaction with haloheteroaromatics using Buchwaid's Cy-JohnPhos and XPhos ligands is reported. The methodology has allowed the fast preparation of highly valuable 4-pyridinyl- and 4-thiazolyl-2-ketothiazoles as common subunits of thiopeptide antibiotics. As direct applications, novel concise syntheses of a sulfomycinamate thio-analogue as well as micrococcinate and saramycetate esters are described.
• Synthesis of saramycetic acid
  作者：Christian Glover、Eleanor A. Merritt、Mark C. Bagley

  DOI：10.1016/j.tetlet.2007.07.111

  日期：2007.9

  The first reported synthesis of saramycetic acid, a degradation product of the complex thiopeptide antibiotic cyclothiazomycin, is achieved in nine steps and 11% overall yield from diethoxyacetonitrile by a strategy, which incorporates two Hantzsch thiazole syntheses using thioamides prepared from the corresponding nitriles without the use of gaseous H2S. The synthetic material was transformed to methyl saramycetate, which had spectroscopic Properties in excellent agreement with the literature data. (c) 2007 Elsevier Ltd. All rights reserved.
• An RNA polymerase inhibitor, cyclothiazomycin B1, and its isomer
  作者：Masaru Hashimoto、Takanori Murakami、Katsuyuki Funahashi、Takashi Tokunaga、Ken-ichi Nihei、Toshikatsu Okuno、Takatsugu Kimura、Hideo Naoki、Hyouta Himeno

  DOI：10.1016/j.bmc.2006.09.006

  日期：2006.12

  Novel cyclic thiopeptides, cyclothiazomycins B1 (1) and B2 (2), were isolated from Streptomyces sp. A307 as potent hyphal swelling inducing substances. They are stable in the solid state but slowly isomerize with one another in solution. Degradation experiments and spectroscopic analyses disclosed that they comprise unique tricyclic structures each containing a dehydroalanine, and two dehydrohomoalanine residues, along with three thiazolines, three thiazoles, and a trisubstituted pyridine. Cyclothiazomycin B1 (1) is expected to be a powerful tool for DNA-RNA transcription studies, because this cyclopeptide inhibits DNA-dependent RNA synthesis by bacteriophage RNA polymerases. (c) 2006 Elsevier Ltd. All rights reserved.