2-[(18S,25S,35S)-35-[(S)-hydroxy(phenyl)methyl]-28-(methoxymethyl)-21-methyl-18-[2-(methylamino)-2-oxoethyl]-16,23,30,33-tetraoxo-25-propan-2-yl-3,13,20,27,37-pentathia-7,17,24,31,34,39,40,41,42,43-decazaheptacyclo[34.2.1.12,5.112,15.119,22.126,29.06,11]tritetraconta-1(38),2(43),4,6(11),7,9,12(42),14,19(41),21,26(40),28,36(39)-tridecaen-8-yl]-1,3-thiazole-4-carbonyl azide | 960061-69-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 2-[(18S,25S,35S)-35-[(S)-hydroxy(phenyl)methyl]-28-(methoxymethyl)-21-methyl-18-[2-(methylamino)-2-oxoethyl]-16,23,30,33-tetraoxo-25-propan-2-yl-3,13,20,27,37-pentathia-7,17,24,31,34,39,40,41,42,43-decazaheptacyclo[34.2.1.12,5.112,15.119,22.126,29.06,11]tritetraconta-1(38),2(43),4,6(11),7,9,12(42),14,19(41),21,26(40),28,36(39)-tridecaen-8-yl]-1,3-thiazole-4-carbonyl azide
• CAS: 960061-69-2
• 化学式: C₄₈H₄₃N₁₅O₈S₆
• 分子量: 1150.36
• InChiKey: KRQXIKYZZHRJQS-BMHVMUFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  77
• 可旋转键数：
  9
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  466
• 氢给体数：
  6
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  2-[(18S,25S,35S)-35-[(S)-hydroxy(phenyl)methyl]-28-(methoxymethyl)-21-methyl-18-[2-(methylamino)-2-oxoethyl]-16,23,30,33-tetraoxo-25-propan-2-yl-3,13,20,27,37-pentathia-7,17,24,31,34,39,40,41,42,43-decazaheptacyclo[34.2.1.12,5.112,15.119,22.126,29.06,11]tritetraconta-1(38),2(43),4,6(11),7,9,12(42),14,19(41),21,26(40),28,36(39)-tridecaen-8-yl]-1,3-thiazole-4-carbonyl azide 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 7.83h， 生成 [(S)-[(18S,25S,35S)-8-(4-formamido-1,3-thiazol-2-yl)-28-(methoxymethyl)-21-methyl-18-[2-(methylamino)-2-oxoethyl]-16,23,30,33-tetraoxo-25-propan-2-yl-3,13,20,27,37-pentathia-7,17,24,31,34,39,40,41,42,43-decazaheptacyclo[34.2.1.12,5.112,15.119,22.126,29.06,11]tritetraconta-1(38),2(43),4,6(11),7,9,12(42),14,19(41),21,26(40),28,36(39)-tridecaen-35-yl]-phenylmethyl] acetate
  参考文献：
  名称：

  天然产物GE2270 A的4-氨基噻唑基类似物的抗菌优化：环烷基羧酸的鉴定

  摘要：

  设计，合成和优化了抗生素天然产物GE2270 A（1）的4-氨基噻唑类似物，以抵抗革兰氏阳性细菌感染。优化工作着重于提高4-氨基噻唑基天然产物模板的理化性质（例如，水溶性和化学稳定性），同时提高体外和体内的抗菌活性。定义了结构活性关系，并且溶解度和功效谱比以前的类似物和1有所改善。这些研究确定了具有环烷基羧酸侧链的新型，有效，可溶和有效的伸长因子Tu抑制剂，并最终选择了开发候选酰胺48。和氨基甲酸酯58。

  DOI：

  10.1021/jm200938f
• 作为产物：
  描述：

  在 sodium azide 作用下， 以 丙酮 为溶剂， 反应 1.33h， 生成 2-[(18S,25S,35S)-35-[(S)-hydroxy(phenyl)methyl]-28-(methoxymethyl)-21-methyl-18-[2-(methylamino)-2-oxoethyl]-16,23,30,33-tetraoxo-25-propan-2-yl-3,13,20,27,37-pentathia-7,17,24,31,34,39,40,41,42,43-decazaheptacyclo[34.2.1.12,5.112,15.119,22.126,29.06,11]tritetraconta-1(38),2(43),4,6(11),7,9,12(42),14,19(41),21,26(40),28,36(39)-tridecaen-8-yl]-1,3-thiazole-4-carbonyl azide
  参考文献：
  名称：

  4-Aminothiazolyl Analogues of GE2270 A: Antibacterial Lead Finding

  摘要：

  4-Aminothiazolyl analogues of the antibacterial natural product GE2270 A (1) were designed, synthesized, and evaluated for Gram positive bacteria growth inhibition. The aminothiazole-based chemical template was evaluated for chemical stability, and its decomposition revealed a novel, structurally simplified, des-thiazole analogue of 1. Subsequent stabilization of the 4-aminothiazolyl functional motif was achieved and initial structure activity relationships defined.

  DOI：

  10.1021/jm101602q

文献信息

• EFTU INHIBITORS OR AMINOTHIAZOLES AND THEIR USES
  申请人：LaMarche Matthew J.

  公开号：US20080221142A1

  公开（公告）日：2008-09-11

  The present application describes organic compounds that are useful for the treatment, prevention and/or amelioration of diseases.

  本申请描述了对治疗、预防和/或改善疾病有用的有机化合物。
• Aminothiazoles and their Uses
  申请人：Bushell Simon

  公开号：US20090156628A1

  公开（公告）日：2009-06-18

  The present application describes organic compounds that are useful for the treatment, prevention and/or amelioration of diseases particularly bacterial infections.

  本申请描述了对治疗、预防和/或改善疾病特别是细菌感染有用的有机化合物。
• Aminothiazoles and their uses
  申请人：Bushell Simon

  公开号：US08426356B2

  公开（公告）日：2013-04-23

  The present application describes organic compounds that are useful for the treatment, prevention and/or amelioration of diseases particularly bacterial infections.

  本申请描述了一些有机化合物，用于治疗、预防和/或改善疾病，特别是细菌感染。
• AMINOTHIAZOLES AND THEIR USES
  申请人：LaMarche Matthew J.

  公开号：US20100267757A1

  公开（公告）日：2010-10-21

  The present application describes organic compounds that are useful for the treatment, prevention and/or amelioration of diseases.

  本申请描述了有机化合物，可用于治疗、预防和/或改善疾病。
• 4-Aminothiazolyl Analogues of GE2270 A: Antibacterial Lead Finding
  作者：Matthew J. LaMarche、Jennifer A. Leeds、JoAnne Dzink-Fox、Karl Gunderson、Philipp Krastel、Klaus Memmert、Michael A. Patane、Elin M. Rann、Esther Schmitt、Stacey Tiamfook、Bing Wang

  DOI：10.1021/jm101602q

  日期：2011.4.14

  4-Aminothiazolyl analogues of the antibacterial natural product GE2270 A (1) were designed, synthesized, and evaluated for Gram positive bacteria growth inhibition. The aminothiazole-based chemical template was evaluated for chemical stability, and its decomposition revealed a novel, structurally simplified, des-thiazole analogue of 1. Subsequent stabilization of the 4-aminothiazolyl functional motif was achieved and initial structure activity relationships defined.