thiazomycin | 905946-70-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: thiazomycin
• 英文别名: 2-[(1S,18S,21E,28S,29S,30S)-30-[[(3aR,4S,6S,7aS)-3,4,7a-trimethyl-3a,4,6,7-tetrahydro-2H-pyrano[3,4-d][1,3]oxazol-6-yl]oxy]-9,52-dihydroxy-18-[(1R)-1-hydroxyethyl]-21-(1-methoxyethylidene)-16,19,26,31,42,46-hexaoxo-32,43,54-trioxa-3,13,23,49-tetrathia-7,17,20,27,45,51,52,55,56,57-decazadecacyclo[26.16.6.229,40.12,5.112,15.122,25.138,41.147,50.06,11.034,39]heptapentaconta-2(57),4,6,8,10,12(56),14,22(55),24,34(39),35,37,40,47,50-pentadecaen-8-yl]-N-(3-amino-3-oxoprop-1-en-2-yl)-1,3-thiazole-4-carboxamide
• CAS: 905946-70-5
• 化学式: C₆₁H₅₈N₁₄O₁₈S₅
• 分子量: 1435.54
• InChiKey: GYOHFSLEKIIJMU-UMNFMQIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  98
• 可旋转键数：
  8
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  575
• 氢给体数：
  9
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  thiazomycin 在 盐酸羟胺 、 水 作用下， 以 溶剂黄146 为溶剂， 反应 7.0h， 生成 N-(3-amino-3-oxoprop-1-en-2-yl)-2-[(1S,18S,21E,28S,29S,30S)-9,52-dihydroxy-30-[(2S,4S,5R,6S)-4-hydroxy-4,6-dimethyl-5-(methylamino)oxan-2-yl]oxy-18-[(1R)-1-hydroxyethyl]-21-(1-methoxyethylidene)-16,19,26,31,42,46-hexaoxo-32,43,54-trioxa-3,13,23,49-tetrathia-7,17,20,27,45,51,52,55,56,57-decazadecacyclo[26.16.6.229,40.12,5.112,15.122,25.138,41.147,50.06,11.034,39]heptapentaconta-2(57),4,6,8,10,12(56),14,22(55),24,34(39),35,37,40,47,50-pentadecaen-8-yl]-1,3-thiazole-4-carboxamide
  参考文献：
  名称：

  Antibiotic compounds

  摘要：

  本发明涉及一种新型噻唑肽类抗生素，能够治疗哺乳动物，特别是人类的严重细菌感染。其中一些类似物还可以作为多功能中间体，用于制备具有有用抗菌活性的新衍生物。

  公开号：

  US20080242597A1
• 作为产物：
  描述：

  nocathiacin I 在 氧气 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 以64%的产率得到thiazomycin
  参考文献：
  名称：

  N-Demethylation of nocathiacin I via photo-oxidation

  摘要：

  In order to improve aqueous solubility of nocathiacin I (1), a potent antibacterial agent, N-demethylation of the amino-sugar moiety was sought. Irradiation of 1 in DMF/CH(2)Cl(2) with UV light of 380 nm led to a cyclic product 2, which was hydrolyzed to yield the desired nocathiacin VI (3). Treatment of 1 with shorter UV light caused trans-cis isomerization of a c-c double bond. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.112

文献信息

• Antibiotic Compound
  申请人：Barrett F. John

  公开号：US20080096856A1

  公开（公告）日：2008-04-24

  Fermentation of a nutrient medium with a Nocardia spp. yields a novel broad spectrum antibiotic compound of structural formula (I) or a pharmaceutically acceptable salt, ester, enantiomer, diasteriomer or mixture.
• Antibiotic compounds
  申请人：Liu Kun

  公开号：US20080242597A1

  公开（公告）日：2008-10-02

  The present invention relates to novel thiazolyl peptide antibiotics capable of treating serious bacterial infections in mammals, and particularly, in humans. Some of the analogs can also be versatile intermediates for the preparation of new derivatives with useful antibacterial activity.

  本发明涉及一种新型噻唑肽类抗生素，能够治疗哺乳动物，特别是人类的严重细菌感染。其中一些类似物还可以作为多功能中间体，用于制备具有有用抗菌活性的新衍生物。
• N-Demethylation of nocathiacin I via photo-oxidation
  作者：Wenying Li、Stella Huang、Xiaohong Liu、John E. Leet、Joseph L. Cantone、Kin S. Lam

  DOI：10.1016/j.bmcl.2008.05.112

  日期：2008.7

  In order to improve aqueous solubility of nocathiacin I (1), a potent antibacterial agent, N-demethylation of the amino-sugar moiety was sought. Irradiation of 1 in DMF/CH(2)Cl(2) with UV light of 380 nm led to a cyclic product 2, which was hydrolyzed to yield the desired nocathiacin VI (3). Treatment of 1 with shorter UV light caused trans-cis isomerization of a c-c double bond. (c) 2008 Elsevier Ltd. All rights reserved.