S-(methylthiomethyl)-D-cysteine methyl ester hydrochloride | 56010-94-7

• 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: S-(methylthiomethyl)-D-cysteine methyl ester hydrochloride
• 英文别名: S-<(Methylthio)methyl>-L-cysteine Methyl Ester Hydrochloride；S-(methylthiomethyl)-L-cysteine methyl ester hydrochloride；S-[(Methylthio)methyl]-L-cysteine Methyl Ester Hydrochloride
• CAS: 56010-94-7
• 化学式: C₆H₁₃NO₂S₂*ClH
• 分子量: 231.768
• InChiKey: GBLDARNXBZBCKP-JEDNCBNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.32
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  S-(methylthiomethyl)-D-cysteine methyl ester hydrochloride 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 生成 S-<(methylthio)methyl>-L-cysteinol
  参考文献：
  名称：

  Pyrimidinylpropenamides as antitumor agents. Analogs of the antibiotic sparsomycin

  摘要：

  A series of pyrimidinylpropenamides 9 and their oxidation products 10 was prepared, as analogues of sparsomycin (1), for antitumor evaluation. Syntheses involved condensation of the appropriate amino alcohol 5 with acid 8. The resulting sulfides 9 were then oxidized with NaIO4 or H2O2 to sulfoxides 10. Activity was studied in lymphocytic leukemia P-338 and KB cell culture. With the exception of the n-decyl analogue, all of the deoxygenated compounds 9 were inactive regardless of the stereochemical form. In the sulfoxide series 10, those compounds prepared with an L configuration at the asymmetric carbon were also inactive. The completely racemic sulfoxides, on the other hand, displayed substantial antitumor activity (ILS = 37-61% in P-388; ED50 = 1.2-2.4 mug/ml in KB) suggesting that both the presence of a sulfoxide moiety and a D configuration at the chiral carbon atom were structural requirements for a positive antitumor response. There appeared to be a large tolerance for the group substituted at the sulfoxide moiety, however.

  DOI：

  10.1021/jm00213a004
• 作为产物：
  描述：

  甲醇 、 S-(methylthiomethyl)-L-cysteine 在 氯化亚砜 作用下， 以87%的产率得到S-(methylthiomethyl)-D-cysteine methyl ester hydrochloride
  参考文献：
  名称：

  Total synthesis of the antibiotic sparsomycin, a modified uracil amino acid monoxodithioacetal

  摘要：

  DOI：

  10.1021/jo00329a027

文献信息

• Biosynthesis of the antitumor antibiotic sparsomycin
  作者：Ronald J. Parry、Yan Li、Elizabeth Eudy Gomez

  DOI：10.1021/ja00041a007

  日期：1992.7

  The biosynthesis of the antitumor antibiotic sparsomycin (1) has been investigated by administration of isotopically labeled precursors to Streptomyces sparsogenes var. sparsogenes. These studies indicated that the dithioacetal moiety (2) of sparsomycin is derived from L-cysteine via the intermediacy of 5-methylcysteine and S-(methylthiomethyl)cysteine, with reduction of the carboxyl group of 5-(m

  已经通过向 Streptomyces sparsogenes var. 施用同位素标记的前体研究了抗肿瘤抗生素稀疏霉素 (1) 的生物合成。生成素。这些研究表明，稀疏霉素的二硫缩醛部分 (2) 是通过 5-甲基半胱氨酸和 S-(甲硫基甲基) 半胱氨酸的中间体从 L-半胱氨酸衍生而来的，5-(甲硫基甲基) 半胱氨酸的羧基在与尿嘧啶部分 (3)。对稀疏霉素尿嘧啶部分 (3) 来源的调查表明，它是通过一个涉及氨基酸两个环的侧链丢失和氧化开环的过程从 L-色氨酸中衍生出来的。yV-甲酰基邻氨基苯甲酸在该过程中的中间体被排除。
• Preparation of amides and esters of the antibiotic bruneomycin and examination of their cytotoxic and antiretroviral activity
  作者：V. V. Tolstikov、N. V. Kozlova、I. V. Yartseva、Ya. V. Dobrynin、E. A. Sinyagina、T. G. Nikolaeva、V. E. Fin'ko、A. A. Arutyunyan、R. G. Melik-Ogandzhanyan、M. N. Preobrazhenskaya

  DOI：10.1007/bf00766862

  日期：1990.2