(R)-2-benzylcysteine hydrochloride

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (R)-2-benzylcysteine hydrochloride
• 英文别名: bencylcysteine hydrochloride；(2R)-2-amino-2-benzyl-3-sulfanylpropanoic acid;hydrochloride
• 化学式: C₁₀H₁₃NO₂S*ClH
• 分子量: 247.746
• InChiKey: APQCNURVMQHIGW-PPHPATTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.3
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-benzylcysteine hydrochloride 、 tert-butyl ((4-cyanothiazol-2-yl)methyl)carbamate 在 水 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以52%的产率得到(4R)-benzyl-2-(2-tert-butoxycarbonylaminomethyl-thiazol-4-yl)-4,5-dihydrothiazole-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and Biological Characterization of the Histone Deacetylase Inhibitor Largazole and C7- Modified Analogues

  摘要：

  Largazole 4a and analogues with modifications at the C7 position, as well as 2,4'-bithiazole 5a, have been synthesized using an acyclic cross-metathesis of the corresponding depsipeptide structures assembled by N-C6(O) or C15(O)-N lactam formation. Similar to the parent system 4a, the series of largazole depsipeptides 4b-d, but not 2,4'-bithiazole 5a, showed a marked inhibition of recombinant HDAC1 and selectivity over HDAC4, as well as strong pro-apoptotic effects on the NB4 leukemia cell line, but they failed to induce differentiation to mature granulocytes. Functional assays of the analogues correlated with the in vitro activities, as shown by increased H3 and a-tubulin acetylation levels and p21(WAF1/C1P1) up-regulation in NB4 cells. The activity of the natural product HDACi largazole 4a is not significantly altered by the presence of groups of different size (H, Et, Ph) at C7 on the dihydrothiazole ring.

  DOI：

  10.1021/jm100244y
• 作为产物：
  描述：

  2R,4R-methyl 2-tert-butyl-1,3-thiazolidine-3-formyl-4-benzyl-4-carboxylate 在 盐酸 作用下， 反应 72.0h， 以91%的产率得到(R)-2-benzylcysteine hydrochloride
  参考文献：
  名称：

  对映选择性合成2-烷基取代的半胱氨酸

  摘要：

  在-90°C下用LDA-DMPU处理衍生自（R-半胱氨酸甲酯盐酸盐和新戊醛的噻唑烷加合物的N-甲酰基衍生物），然后与碘甲烷反应，生成相应的甲基化的噻唑烷，其中含有甲基和叔丁基基团实际上仅抗- 。在5M HCl存在下，然后得到（彼此水解- [R。-2-甲基半胱氨酸盐酸盐的优良率和对映体纯度优异的光学纯度的其它2-烷基取代的半胱氨酸的范围是由本变形例中制备的Seebach的“手性的自我复制”协议。

  DOI：

  10.1016/s0040-4020(01)86313-4

文献信息

• Enantioselective Synthesis of 2-alkyl substituted cysteines
  作者：Gerald Pattenden、Stephen M. Thom、Martin F. Jones

  DOI：10.1016/s0040-4020(01)86313-4

  日期：1993.3

  Treatment of the N-formyl derivative of the thiazolidine adduct derived from (R-cysteine methyl ester hydrochloride and pivalaldehyde, with LDA-DMPU at −90°C, followed by reaction with iodomethane produces the corresponding methylated thiazolidine containing the methyl and t-butyl groups virtually exclusively anti- to one another. Hydrolysis in the presence of 5M HCl then affords (R-2-methylcysteine

  在-90°C下用LDA-DMPU处理衍生自（R-半胱氨酸甲酯盐酸盐和新戊醛的噻唑烷加合物的N-甲酰基衍生物），然后与碘甲烷反应，生成相应的甲基化的噻唑烷，其中含有甲基和叔丁基基团实际上仅抗- 。在5M HCl存在下，然后得到（彼此水解- [R。-2-甲基半胱氨酸盐酸盐的优良率和对映体纯度优异的光学纯度的其它2-烷基取代的半胱氨酸的范围是由本变形例中制备的Seebach的“手性的自我复制”协议。
• Synthesis and Biological Characterization of the Histone Deacetylase Inhibitor Largazole and C7- Modified Analogues
  作者：José A. Souto、Esther Vaz、Ilaria Lepore、Ann-Christin Pöppler、Gianluigi Franci、Rosana Álvarez、Lucia Altucci、Ángel R. de Lera

  DOI：10.1021/jm100244y

  日期：2010.6.24

  Largazole 4a and analogues with modifications at the C7 position, as well as 2,4'-bithiazole 5a, have been synthesized using an acyclic cross-metathesis of the corresponding depsipeptide structures assembled by N-C6(O) or C15(O)-N lactam formation. Similar to the parent system 4a, the series of largazole depsipeptides 4b-d, but not 2,4'-bithiazole 5a, showed a marked inhibition of recombinant HDAC1 and selectivity over HDAC4, as well as strong pro-apoptotic effects on the NB4 leukemia cell line, but they failed to induce differentiation to mature granulocytes. Functional assays of the analogues correlated with the in vitro activities, as shown by increased H3 and a-tubulin acetylation levels and p21(WAF1/C1P1) up-regulation in NB4 cells. The activity of the natural product HDACi largazole 4a is not significantly altered by the presence of groups of different size (H, Et, Ph) at C7 on the dihydrothiazole ring.