methyl saramycetate | 76706-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl saramycetate
• 英文别名: Methyl 2-(2-acetyl-1,3-thiazol-4-yl)-1,3-thiazole-4-carboxylate
• CAS: 76706-68-8
• 化学式: C₁₀H₈N₂O₃S₂
• 分子量: 268.317
• InChiKey: PFGGIYDQUWLLQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl saramycetate 在 pyridinium hydrobromide perbromide 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 6.5h， 生成 methyl 3-(2,4':2',4''-terthiazole-4-carboxamido)propyl sulfide
  参考文献：
  名称：

  博来霉素类似物。与博来霉素a 2相关的噻唑酰胺的合成和质子核磁共振谱归属

  摘要：

  描述了一系列3-氨基丙基二甲基s氯化物的2-取代的噻唑-4-羧酰胺的合成，并对这些衍生物的质子核磁共振谱进行了表征。该化合物是抗肿瘤抗生素博来霉素A 2的DNA结合部分的片段和类似物，将在该家族药物中用作构效关系的探针。

  DOI：

  10.1002/jhet.5570180629
• 作为产物：
  描述：

  3-乙酰氨基硫代丙酰胺 在 chromium(VI) oxide 、 sodium hydroxide 、 硫酸 、 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 4.58h， 生成 methyl saramycetate
  参考文献：
  名称：

  Synthesis of Ozonolysis Products of Myxothiazol.

  摘要：

  通过应用 Hantzsch 噻唑程序，合成了与 myxothiazol 降解产物相对应的双噻唑衍生物（2 和 (±)-3）。利用脂肪酶在水饱和有机溶剂中对相应的醋酸盐（(±)-18、(±)-20 和 (±)-21）进行对映选择性水解，得到了具有光学活性的 (S)-3 (87-88% ee) 及其类似物 (S)-16 (91% ee)。

  DOI：

  10.1248/cpb.42.1208

文献信息

• 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.
• Bleomycin analogs. Synthesis and proton nmr spectral assignments of thiazole amides related to bleomycin a₂
  作者：James M. Riordan、Ted T. Sakai

  DOI：10.1002/jhet.5570180629

  日期：1981.10

  The synthesis of a series of 2-substituted thiazole-4-carboxamides of 3-aminopropyldimethylsulfonium chloride is described and the proton nmr spectral assignments of these derivatives are made. The compounds, which are fragments and analogs of the DNA-binding portion of the antitumor antibiotic bleomycin A2, will serve as probes of structure-activity relationships in this family of drugs.

  描述了一系列3-氨基丙基二甲基s氯化物的2-取代的噻唑-4-羧酰胺的合成，并对这些衍生物的质子核磁共振谱进行了表征。该化合物是抗肿瘤抗生素博来霉素A 2的DNA结合部分的片段和类似物，将在该家族药物中用作构效关系的探针。
• Synthesis of Ozonolysis Products of Myxothiazol.
  作者：Hiroyuki AKITA、Masako NOZAWA、Shinji NAGUMO

  DOI：10.1248/cpb.42.1208

  日期：——

  By applying the Hantzsch thiazole procedure, the synthesis of bithiazole derivatives (2 and (±)-3) corresponding to degradation products of myxothiazol was achieved. Optically active (S)-3 (87-88% ee) and its analog (S)-16(91% ee) were obtained through enantioselective hydrolysis of the corresponding acetates ((±)-18, (±)-20 and (±)-21) using lipase in water-saturated organic solvent.

  通过应用 Hantzsch 噻唑程序，合成了与 myxothiazol 降解产物相对应的双噻唑衍生物（2 和 (±)-3）。利用脂肪酶在水饱和有机溶剂中对相应的醋酸盐（(±)-18、(±)-20 和 (±)-21）进行对映选择性水解，得到了具有光学活性的 (S)-3 (87-88% ee) 及其类似物 (S)-16 (91% ee)。