(5S)-5-azido-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene | 277749-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (5S)-5-azido-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene
• 英文别名: 4-[(1E,3S,5Z)-3-azido-6-iodo-2-methylhepta-1,5-dienyl]-2-methyl-1,3-thiazole
• CAS: 277749-36-7
• 化学式: C₁₂H₁₅IN₄S
• 分子量: 374.248
• InChiKey: QRGSQQNFPJRCDP-ITOCJQPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S)-5-azido-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 (1E,3S,5Z)-6-iodo-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hepta-1,5-dien-3-amine
  参考文献：
  名称：

  On the Interactivity of Complex Synthesis and Tumor Pharmacology in the Drug Discovery Process:  Total Synthesis and Comparative in Vivo Evaluations of the 15-Aza Epothilones

  摘要：

  The total syntheses of 12,13,15-desoxy-15(S)-aza-epothilone B (aza-dEpoB; dEpoB-lactam) and 12,13, 15-desoxy-15(R)-aza-epothilone B (15-epi-aza-dEpoB; 15-epi-dEpoB-lactam) have been accomplished via a highly convergent strategy. We have also successfully oxidized 12,13,15-desoxy 15(S)-aza-epothilone B to aza-epothilone B (aza-EpoB; EpoB-lactam). Aza-epothilone B has been advanced to phase I clinical trials by the Bristol-Myers Squibb group. Our synthesis is efficient and was amenable to the production of significant quantities of these lactams. Using our fully synthetically derived lactams, in vitro and in vivo studies were conducted in comparison with advanced clinical candidates, 12,13-desoxyepothilone B and 12,13-desoxyepothilone F, also derived by total synthesis.

  DOI：

  10.1021/jo010275c
• 作为产物：
  描述：

  triethyl-[(1E,3R,5Z)-6-iodo-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hepta-1,5-dien-3-yl]oxysilane 在 三(2-氯乙基)胺 、 偶氮二甲酸二异丙酯 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 (5S)-5-azido-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene
  参考文献：
  名称：

  On the Total Synthesis and Preliminary Biological Evaluations of 15(R) and 15(S) Aza-dEpoB:  A Mitsunobu Inversion at C15 in Pre-Epothilone Fragments

  摘要：

  [GRAPHICS]The syntheses of two epothilone analogues, 15(S)-aza-12,13-desoxyepothilone B and the epimeric 15(R)-aza-12,13-desoxyepothitone B, are described. A Mitsunobu inversion was utilized for elaboration of pre epothilone fragments to the corresponding macrolactam. Tubulin binding and cytotoxicity profiles of these analogues are presented.

  DOI：

  10.1021/ol005932m

文献信息

• Epothilone derivatives and methods for making and using the same
  申请人：——

  公开号：US20030045711A1

  公开（公告）日：2003-03-06

  This invention relates to compounds of formula (I) 1 and to pharmaceutically acceptable salts and solvates thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , W, X, Y, and Ar are as defined herein. Compounds of formula (I) are useful in the treatment of diseases or conditions characterized by cellular hyperproliferation. This invention also relates to means for the preparation of compounds of formula (I); formulations containing compounds of formula (I); and methods for the use of said compounds and formulations in the treatment of a disease or condition characterized by cellular hyperproliferation, including cancer.

  这项发明涉及公式（I）的化合物及其药用可接受的盐和溶剂化合物，其中R1、R2、R3、R4、R5、W、X、Y和Ar的定义如本文所述。公式（I）的化合物在治疗细胞过度增殖引起的疾病或症状方面是有用的。这项发明还涉及制备公式（I）化合物的方法；含有公式（I）化合物的配方；以及使用所述化合物和配方治疗细胞过度增殖引起的疾病或症状，包括癌症的方法。
• 伊沙匹隆全合成
  申请人：深圳市佳泰药业股份有限公司

  公开号：CN103275091A

  公开（公告）日：2013-09-04

  本发明属于药物合成技术领域，具体涉及一种伊沙匹隆的中间体、全合成方法以及用途。该化合物具有如下结构式1： 。
• J. Org. Chem. 2001, 66, 4369-4378
  作者：

  DOI：——

  日期：——
• US6489314B1
  申请人：——

  公开号：US6489314B1

  公开（公告）日：2002-12-03
• US6589968B2
  申请人：——

  公开号：US6589968B2

  公开（公告）日：2003-07-08