(3S)-3-hydroxy-1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]pent-4-en-1-one | 790661-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3S)-3-hydroxy-1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]pent-4-en-1-one
• CAS: 790661-44-8
• 化学式: C₁₁H₁₇NO₂S₂
• 分子量: 259.393
• InChiKey: QRJWZESGUWVTJK-RKDXNWHRSA-N

物化性质

• 沸点：
  379.1±52.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (R)-2'-(aminomethyl)-4-methyl-4,5-dihydro-[2,4'-bithiazole]-4-carboxylate 2,2,2-trifluoroacetate 、 (3S)-3-hydroxy-1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]pent-4-en-1-one 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以59 mg的产率得到methyl (4R)-2-[2-[[[(3S)-3-hydroxypent-4-enoyl]amino]methyl]-1,3-thiazol-4-yl]-4-methyl-5H-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  组蛋白脱乙酰酶抑制剂拉格唑的总合成和分子靶点

  摘要：

  描述了简洁和收敛的合成（八个步骤，总产率为 19%）的全部细节，其扩展到一系列关键类似物的制备，以及拉格唑的分子靶点和药效团。拉格唑合成的核心是形成紧张的 16 元缩酚肽核心的大环化反应，然后是用于安装硫酯的烯烃交叉复分解反应。拉格唑及其关键类似物的生物学评价，包括乙酰类似物、硫醇类似物和羟基类似物，表明组蛋白脱乙酰酶 (HDAC) 是拉格唑的分子靶点，拉格唑是 I 类 HDAC 抑制剂。此外，构效关系 (SAR) 研究表明，硫醇基团是天然产物的药效团。拉格唑'

  DOI：

  10.1021/ja8013727
• 作为产物：
  描述：

  (R)-1-(4-异丙基-2-硫氧代噻唑啉-3-基)乙酮 、 丙烯醛 在 四氯化钛 、 鹰爪豆碱 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (3S)-3-hydroxy-1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]pent-4-en-1-one 、 (3R)-3-Hydroxy-1-[(4S)-4-(1-methylethyl)-2-thioxo-3-thiazolidinyl]-4-penten-1-one
  参考文献：
  名称：

  Stereoselective aldol additions of titanium enolates of N-acetyl-4-isopropyl-thiazolidinethione

  摘要：

  The addition of chlorotitanium enolates of N-acetyl isopropyl thiazolidine-2-thione to aldehydes was investigated. The stereoselectivity of the aldol products was controlled by the number of equivalents of base added. The syn aldol product was obtained preferentially when 2 equiv of Lewis acid and 1 equiv of base were employed. The anti aldol product was obtained preferentially when 1 equiv of Lewis acid and 2 equiv of base were employed for unsaturated aldehydes. Unexpected results were found with hindered aldehydes when 2 equiv of base were employed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.008

文献信息

• [EN] METHODS OF PREPARATION OF MACROCYCLIC COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS MACROCYCLIQUES
  申请人：UNIV FLORIDA

  公开号：WO2009105284A1

  公开（公告）日：2009-08-27

  The instant invention describes methods for producing macrocyclic compounds having antiproliferation activity, and useful in methods of treating disorders such as cancer, tumors and cell proliferation related disorders.

  这项即时发明描述了生产具有抗增殖活性的大环化合物的方法，这些化合物在治疗癌症、肿瘤和与细胞增殖有关的疾病的方法中非常有用。
• METHODS OF PREPARATION OF MACROCYCLIC COMPOUNDS
  申请人：Luesch Hendrik

  公开号：US20110092697A1

  公开（公告）日：2011-04-21

  The instant invention describes methods for producing macrocyclic compounds having antiproliferation activity, and useful in methods of treating disorders such as cancer, tumors and cell proliferation related disorders.
• US8759512B2
  申请人：——

  公开号：US8759512B2

  公开（公告）日：2014-06-24
• Stereoselective aldol additions of titanium enolates of N-acetyl-4-isopropyl-thiazolidinethione
  作者：Mathis B. Hodge、Horacio F. Olivo

  DOI：10.1016/j.tet.2004.08.008

  日期：2004.10

  The addition of chlorotitanium enolates of N-acetyl isopropyl thiazolidine-2-thione to aldehydes was investigated. The stereoselectivity of the aldol products was controlled by the number of equivalents of base added. The syn aldol product was obtained preferentially when 2 equiv of Lewis acid and 1 equiv of base were employed. The anti aldol product was obtained preferentially when 1 equiv of Lewis acid and 2 equiv of base were employed for unsaturated aldehydes. Unexpected results were found with hindered aldehydes when 2 equiv of base were employed. (C) 2004 Elsevier Ltd. All rights reserved.
• Total Synthesis and Molecular Target of Largazole, a Histone Deacetylase Inhibitor
  作者：Yongcheng Ying、Kanchan Taori、Hyoungsu Kim、Jiyong Hong、Hendrik Luesch

  DOI：10.1021/ja8013727

  日期：2008.7.1

  Full details of the concise and convergent synthesis (eight steps, 19% overall yield), its extension to the preparation of a series of key analogues, and the molecular target and pharmacophore of largazole are described. Central to the synthesis of largazole is a macrocyclization reaction for formation of the strained 16-membered depsipeptide core followed by an olefin cross-metathesis reaction for

  描述了简洁和收敛的合成（八个步骤，总产率为 19%）的全部细节，其扩展到一系列关键类似物的制备，以及拉格唑的分子靶点和药效团。拉格唑合成的核心是形成紧张的 16 元缩酚肽核心的大环化反应，然后是用于安装硫酯的烯烃交叉复分解反应。拉格唑及其关键类似物的生物学评价，包括乙酰类似物、硫醇类似物和羟基类似物，表明组蛋白脱乙酰酶 (HDAC) 是拉格唑的分子靶点，拉格唑是 I 类 HDAC 抑制剂。此外，构效关系 (SAR) 研究表明，硫醇基团是天然产物的药效团。拉格唑'