S-benzyl-L-cysteine benzyl ester | 39801-36-0

• 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-benzyl-L-cysteine benzyl ester
• 英文别名: S-Benzyl-L-cystein-benzylester；S-Benzyl-L-cystein-benzylester-hydrochlorid；S-Benzyl-L-cystein-benzylester；(R)-Benzyl 2-amino-3-(benzylthio)propanoate；benzyl (2R)-2-amino-3-benzylsulfanylpropanoate
• CAS: 39801-36-0
• 化学式: C₁₇H₁₉NO₂S
• 分子量: 301.409
• InChiKey: RWISUDSSXJFKIY-INIZCTEOSA-N

物化性质

• 沸点：
  446.1±45.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-benzyl-L-cysteine benzyl ester 在 四氢呋喃 、 氢溴酸 、 溶剂黄146 、 三乙胺 、 氯甲酸异丁酯 作用下， 生成 S-benzyl-N-L-isoasparaginyl-L-cysteine benzyl ester
  参考文献：
  名称：

  Isoasparagine-oxytocin: The Isoasparagine Isomer of Oxytocin¹

  摘要：

  DOI：

  10.1021/ja01510a039
• 作为产物：
  描述：

  S-苄基-L-半胱氨酸 、 苯甲醇 在 苯磺酸 作用下， 生成 S-benzyl-L-cysteine benzyl ester
  参考文献：
  名称：

  Maclaren et al., Australian Journal of Chemistry, 1958, vol. 11, p. 345,355

  摘要：

  DOI：

文献信息

• Maclaren et al., Australian Journal of Chemistry, 1958, vol. 11, p. 345,355
  作者：Maclaren et al.

  DOI：——

  日期：——
• Hooper et al., Journal of the Chemical Society, 1956, p. 3148,3151
  作者：Hooper et al.

  DOI：——

  日期：——
• Synthesis of Two Protected Hexapeptides Containing the N-Terminal and C-Terminal Sequences of Arginine-Vasopressin¹
  作者：Panayotis G. Katsoyannis、Duane T. Gish、George P. Hess、Vincent Du Vigneaud

  DOI：10.1021/ja01543a051

  日期：1958.5
• <p>13-[CH2CO-Cys-(Bzl)-OBzl]-Berberine: Exploring The Correlation Of Anti-Tumor Efficacy With ROS And Apoptosis Protein</p>
  作者：Guanyu Li、Yi Ren、Xiaoyi Zhang、Shurui Zhao、Yaonan Wang、Jianhui Wu、Shiqi Peng、Ming Zhao

  DOI：10.2147/ott.s231035

  日期：——

  Background: The discovery of novel derivative of berberine (BBR) having higher antitumor activity in vivo is of clinical importance. In this profile, 13-[CH2CO-Cys-(Bzl)-OBzl]-berberine (13-Cys-BBR) was prepared for related assays.Purpose: The object of preparation and evaluation is to show the advantages of 13-Cys-BBR over BBR in both in vitro and in vivo anti-tumor actions, furthermore to correlate the proliferation of cancer cells with ROS formation and anti-apoptosis protein (XIAP) expression inside cancer cells.Methods: Transwell chamber was used to simulate the intestinal and cell wall for bioavailability evaluation; MTT assay was used to evaluate the in vitro anti-proliferation activity; fluorescein isothiocyanate content was used to represent ROS level in HCT-8 cells; Western blot assay was used to quantify the expression of XIAP, caspase-3, and poly ADP-ribose polymerase in HCT-8 cells; and 5180 mouse model was used to evaluate the in vivo antitumor activity.Results: In vitro the IC50 values (similar to 15-40 mu M) of 13-Cys-BBR against the proliferation of eight cancer cell lines were significantly lower than those of BBR (similar to 25-140 mu M); the content of ROS formed inside HCT-8 cells treated by 13-Cys-BBR was similar to 3.44-folds higher than that inside HCT-8 cells treated by BBR; the expression of XIAP in HCT-8 cells treated by 13-Cys-BBR was similar to 1.21-folds lower than that in HCT-8 cells treated by BBR; the tumor weight of 5180 mice orally treated by 2 mu mol/kg/day of 13-Cys-BBR (similar to 1.5 g) was significantly lower than that of 5180 mice orally treated by 2 mu mol/kg/day of BBR (similar to 2.5 g); and the active pocket of XIAP was more suitable for 13-Cys-BBR than for BBR.Conclusion: The anti-tumor action correlates with ROS and apoptosis protein, which suggests 13-Cys-BBR is a promising candidate for preclinical study.
• Gnichtel,H.; Lautsch,W., Chemische Berichte, 1965, vol. 98, p. 1647 - 1654
  作者：Gnichtel,H.、Lautsch,W.

  DOI：——

  日期：——