[(5-氨基-1,3,4-噻二唑-2-基)硫基]乙酸甲酯 | 72836-12-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: [(5-氨基-1,3,4-噻二唑-2-基)硫基]乙酸甲酯
• 中文别名: 2-[(5-氨基-1,3,4-噻二唑-2-基)硫基]乙酸甲酯
• 英文名称: Methyl [(5-amino-1,3,4-thiadiazol-2-YL)thio]acetate
• 英文别名: methyl 2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]acetate
• CAS: 72836-12-5
• 化学式: C₅H₇N₃O₂S₂
• mdl: MFCD01798985
• 分子量: 205.261
• InChiKey: ASSFIPIQXCHMOD-UHFFFAOYSA-N

物化性质

• 沸点：
  370.2±44.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  苯甲酰氯,2-(氯硒代)- 、 [(5-氨基-1,3,4-噻二唑-2-基)硫基]乙酸甲酯 以 乙腈 为溶剂， 反应 2.0h， 以46.5%的产率得到C₁₂H₉N₃O₃S₂Se
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of 1,3,4-thiadiazole derivatives based on benzisoselenazolone

  摘要：

  A series of novel 1,3,4-thiadiazole derivatives based on benzisoselenazolone were synthesized and evaluated for their cytotoxicity in vitro against human liver cancer cell SSMC-7721, human breast cancer cell MCF-7 and human lung cancer cell A549 by CCK-8 assay. The results showed that compounds 7e, 7f, 7h, 7k, 7I and 7m displayed good cytotoxicity against MCF-7 cell lines. Compound 71 exhibited the most potent antitumor activities among the tested compounds. (C) 2012 Bao Quan Chen. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.04.005
• 作为产物：
  描述：

  氯乙酸甲酯 、 2-氨基-5-巯基-1,3,4-噻二唑 以 水 为溶剂， 反应 4.0h， 生成 [(5-氨基-1,3,4-噻二唑-2-基)硫基]乙酸甲酯
  参考文献：
  名称：

  [5-(邻羟基苯基亚甲基亚氨基)-1,3,4-噻二 唑-2-基]硫乙酸酯、制备方法及其应用

  摘要：

  本发明属于化学合成技术领域，提供了一种[5‑(邻羟基苯基亚甲基亚氨基)‑1,3,4‑噻二唑‑2‑基]硫乙酸酯、制备方法及其应用。[5‑(邻羟基苯基亚甲基亚氨基)‑1,3,4‑噻二唑‑2‑基]硫乙酸酯的制备方法，以氯乙酸分别和甲醇、乙醇与正丁醇为原料合成氯乙酸酯，氯乙酸酯进一步与2‑氨基‑5‑巯基‑1,3,4‑噻二唑水相高效合成(5‑氨基‑1,3,4‑噻二唑‑2‑基)硫乙酸酯，(5‑氨基‑1,3,4‑噻二唑‑2‑基)硫乙酸酯再与芳醛缩合得到目标化合物。本发明的合成路线操作简单、节省能源、污染少、反应条件温和，是一种较为合理、理想的方法。

  公开号：

  CN105541757B

文献信息

• Identification of Potent and Novel α4β1 Antagonists Using in Silico Screening
  作者：Juswinder Singh、Herman van Vlijmen、Yusheng Liao、Wen-Cherng Lee、Mark Cornebise、Mary Harris、I-hsiang Shu、Alan Gill、Julio H. Cuervo、William M. Abraham、Steven P. Adams

  DOI：10.1021/jm020054e

  日期：2002.7.1

  The antigen alpha4beta1 (very late antigen-4, VLA-4) plays an important role in the migration of white blood cells to sites of inflammation. It has been implicated in the pathology of a variety of diseases including asthma, multiple sclerosis, and rheumatoid arthritis. We describe a series of potent inhibitors of alpha4beta1 that were discovered using computational screening for replacements of the peptide region of an existing tetrapeptide-based alpha4beta1 inhibitor (1; 4-[N'-(2-methylphenyl)-ureido]phenylacetyl-Leu-Asp-Val) derived from fibronectin. The search query was constructed using a model of 1 that was based upon the X-ray conformation of the related integrin-binding region of vascular cell adhesion molecule-1 (VCAM-1). The 3D search query consisted of the N-terminal cap and the carboxyl side chain of 1 because, upon the basis of existing structure-activity data on this series, these were known to be critical for high-affinity binding to alpha4beta1. The computational screen identified 12 reagents from a virtual library of 8624 molecules as satisfying the model and our synthetic filters. All of the synthesized compounds tested inhibit alpha4beta1 association with VCAM-1, with the most potent compound having an IC50 of 1 nM, comparable to the starting compound. Using CATALYST, a 3D QSAR was generated that rationalizes the variation in activities of these alpha4beta1 antagonists. The most potent compound was evaluated in a sheep model of asthma, and a 30 mg nebulized dose was able to inhibit early and late airway responses in allergic sheep following antigen challenge and prevented the development of nonspecific airway hyperresponsiveness to carbachol. Our results demonstrate that it is possible to rapidly identify nonpeptidic replacements of integrin peptide antagonists, This approach should be useful in identification of nonpeptidic alpha4beta1 inhibitors with improved pharmacokinetic properties relative to their peptidic counterparts.
• MURASE, KIYOSHI;MASE, TOSHIYASU;HARA, HIROMU;TOMIOKA, KENICHI
  作者：MURASE, KIYOSHI、MASE, TOSHIYASU、HARA, HIROMU、TOMIOKA, KENICHI

  DOI：——

  日期：——