S-<(methylthio)methyl>-L-cysteinol | 88001-48-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: S-<(methylthio)methyl>-L-cysteinol
• 英文别名: (2R)-2-amino-3-(methylsulfanylmethylsulfanyl)propan-1-ol
• CAS: 88001-48-3
• 化学式: C₅H₁₃NOS₂
• 分子量: 167.296
• InChiKey: UNCTWCSOFDCGIW-RXMQYKEDSA-N

物化性质

• 沸点：
  324.7±32.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  96.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  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

文献信息

• Structure-activity relationships of sparsomycin and its analogs: octylsparsomycin: The first analog more active than sparsomycin
  作者：Rob M. J. Liskamp、J. Hans Colstee、Harry C. J. Ottenheijm、Peter Lelieveld、Wil Akkerman

  DOI：10.1021/jm00369a012

  日期：1984.3

  Nine analogues of sparsomycin were synthesized, and their cytostatic activity was studied in an in vitro clonogenic L1210 assay by measuring the inhibition of colony formation. The activity of an analogue, expressed as an ID50 value, was compared to that of sparsomycin. Each possesses not more than two structural modifications of the sparsomycin molecule 1. Comparison of the activity of with that of

  合成了9种稀疏霉素的类似物，并在体外克隆形成L1210分析中通过测量菌落形成的抑制作用研究了它们的细胞抑制活性。将类似物的活性（表示为ID50值）与Sparsomycin的活性进行了比较。每个具有不超过两个的稀疏霉素分子1的结构修饰。分别与具有RCSS，SCSS和RCRS手性的立体异构体的活性进行比较，表明手性碳原子的S构型对于最佳活性，而Sparsomycin的亚砜硫原子的R手性很重要。对S-脱氧类似物以及具有β-亚砜功能的化合物的ID 50值的研究表明，α-硫原子上存在氧原子是必不可少的。将反式双键异构化为顺式双键会产生异金石霉素（方案II），其活性较低。Sparsomycin的细胞抑制活性似乎与其亲脂性有关：辛基Sparsomycin被证明是Sparsomycin的三倍。
• Pyrimidinylpropenamides as antitumor agents. Analogs of the antibiotic sparsomycin
  作者：Chie-Chang L. Lin、Ronald J. Dubois

  DOI：10.1021/jm00213a004

  日期：1977.3

  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.