N-benzyloxycarbonyl cystein methyl ester

• 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: N-benzyloxycarbonyl cystein methyl ester
• 英文别名: methyl 2-(benzyloxycarbonylamino)-3-mercaptopropionate；N-benzyloxycarbonyl cysteine methyl ester；Z-Cys-OME；methyl 2-(phenylmethoxycarbonylamino)-3-sulfanylpropanoate
• 化学式: C₁₂H₁₅NO₄S
• 分子量: 269.321
• InChiKey: FEADQZMKQOMOMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl cystein methyl ester 、 beta-D-半乳糖五乙酸酯 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 20.0h， 生成 methyl 2-(benzyloxycarbonylamino)-3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylthio)propionate
  参考文献：
  名称：

  NOVEL GALACTOSYLCERAMIDE ANALOGS AND BETA-GLUCOCEREBROSIDASE ACTIVATORS,EXTERNAL SKIN PREPARATIONS AND METHOD OF ACTIVATING BETA-GLUCOCEREBROSIDASE USING THE ANALOGS

  摘要：

  公开号：

  EP1408045B1
• 作为产物：
  描述：

  N-benzyloxycarbonyl cystine methyl ester 在 indium 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以96%的产率得到N-benzyloxycarbonyl cystein methyl ester
  参考文献：
  名称：

  Vidya Sagar Reddy; Venkat Rao; Iyengar, Synthetic Communications, 2000, vol. 30, # 5, p. 859 - 862

  摘要：

  DOI：

文献信息

• The Selective Deprotection of Thioesters Using Titanium(IV) Chloride/Zinc
  作者：Chung Keun Jin、Hyung Jae Jeong、Min Kyu Kim、Ju Young Kim、Young-Jin Yoon、Sang-Gyeong Lee

  DOI：10.1055/s-2001-18769

  日期：——

  A new method for deprotection of thioesters using TiCl4/Zn at 0-25 °C is described. The procedure chemoselectively cleaves the S-CO bond in thioesters in the presence of other carbonyl functional groups and other protecting groups to cleanly produce thiols.

  描述了一种在0-25°C下使用TiCl4/Zn去保护硫酯的新方法。该过程化学选择性地裂解硫酯中的S-CO键，在存在其他羰基功能团和其他保护基的情况下，干净地产生硫醇。
• 半胱氨酸衍生物及其合成方法
  申请人：上海大学

  公开号：CN112028800B

  公开（公告）日：2022-11-08

  本发明公开了一种半胱氨酸衍生物及其合成方法。本发明方法反应以半胱氨酯和芳基溴作为底物，在催化剂，配体，还原剂，添加剂的作用下，常温下温和反应6‑12小时，得到半胱氨酸衍生物。本发明具有催化剂金属较便宜，原料简单易得，反应温和，一步反应、步骤简单，操作安全，产率较高。
• Novel galactosylceramide analogs, and beta-glucocerebrosidase activators, external skin preparations and method of activating beta-glucocerebrosidase using the analogs
  申请人：——

  公开号：US20040242499A1

  公开（公告）日：2004-12-02

  Galactosylceramide analogues represented by the following formula (1) or (2). 1 (wherein X and Y each represent S or O, R 1 and R 2 each represent an alkyl group or an alkenyl group each having 9 to 35 carbon atoms. R 3 represents an alkyl group or an alkenyl group each having 2 to 30 carbon atoms.) It is provided a &bgr;-glucocerebrosidase activator which is easily available, and external skin preparations and a method of activating &bgr;-glucocerebrosidase, in which improvement in formation of horny layer transmission barrier is expected by activating &bgr;-glucocerebrosidase so that an improved effect in rough skin is also expected.

  提供以下公式（1）或（2）所表示的类似半乳糖鞘氨醇： 其中，X和Y各代表S或O，R1和R2各代表一个有9到35个碳原子的烷基或烯基，R3代表一个有2到30个碳原子的烷基或烯基。提供了一种易于获取的β-葡糖鞘脂酶激活剂，以及激活β-葡糖鞘脂酶的外用皮肤制剂和方法，通过激活β-葡糖鞘脂酶，预期改善角质层传递屏障的形成，从而也预期改善皮肤粗糙的效果。
• Synthesis and structure–activity relationship of new cytotoxic agents targeting human glutathione-S-transferases
  作者：Dante Rotili、Anastasia De Luca、Domenico Tarantino、Silvia Pezzola、Mariantonietta Forgione、Blasco Morozzo della Rocca、Mattia Falconi、Antonello Mai、Anna Maria Caccuri

  DOI：10.1016/j.ejmech.2014.10.033

  日期：2015.1

  The 6((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio)hexan-1-ol (NBDHEX, 1), a "suicide inhibitor" of the glutathione-S-transferase GSTP1-1, showed pro-apoptotic properties in tumor cells, but in vivo studies were limited by poor bioavailability and high affinity towards GSTM2-2, expressed in many non-cancerous tissues. Here we describe the synthesis and biological characterization of new 1 analogs (2-40), in which the hydroxyhexyl portion at the C4-sulfur atom has been replaced with phenyl-containing moieties as well as substituted alkyl chains. Some of the new compounds displayed 10-100 times increased water-solubility (8, 11, 17, 26-28, 34, 35), and most of them showed higher GSTP1-1 selectivity (2-20, 23-26, 31-33, 35) than 1. The presence of a phenyl ring with polar substituents is in general associated, with some exceptions (23, 24) to low cytotoxicity in osteosarcoma U-2OS cells. Differently, some alkyl derivatives possess cytotoxicity comparable (26, 34,35) or higher (30, 32) than 1. Among the novel compounds, selected ones (26, 27, 34, and 35) deserve further investigation for their anticancer potential. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Process for S-Aryl cysteine
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1236715B1

  公开（公告）日：2008-10-15