(4H-1,2,4-三唑-3-基硫基)乙酸 | 24127-58-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: (4H-1,2,4-三唑-3-基硫基)乙酸
• 中文别名: (4H-[1,2,4]三唑-3-基硫基)-乙酸
• 英文名称: 1,2,4-Triazolyl-5-thioacetic acid
• 英文别名: 4H-1,2,4-Triazol-3-thioessigsaeure；(4H-[1,2,4]triazol-3-ylsulfanyl)-acetic acid；1,2,4-triazole-5-ylthioacetic acid；2-(1H-1,2,4-triazol-5-ylsulfanyl)acetic acid
• CAS: 24127-58-0
• 化学式: C₄H₅N₃O₂S
• mdl: MFCD01048972
• 分子量: 159.169
• InChiKey: ZENBUDIZSYJIIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8℃，干燥

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 (4H-1,2,4-三唑-3-基硫基)乙酸 在 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以88%的产率得到6-[1-Phenyl-meth-(Z)-ylidene]-thiazolo[2,3-c][1,2,4]triazol-5-one
  参考文献：
  名称：

  Synthesis and biological activity of 6-ylidenethiazolidino[3,2-c]-1,2,4-triazol-5-ones

  摘要：

  DOI：

  10.1007/bf00779899
• 作为产物：
  描述：

  雷西那得中间体 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以100%的产率得到(4H-1,2,4-三唑-3-基硫基)乙酸
  参考文献：
  名称：

  Rationally designed "dipeptoid" analogs of CCK. Acid mimics of the potent and selective non-peptide CCK-B receptor antagonist (CI-988)

  摘要：

  This paper outlines the synthesis of selected acid mimics of the non-peptide CCK-B selective antagonist CI-988, 1. CCK-B and CCK-A binding affinities of these analogues are described and their CCK-B affinity and selectivity rationalized by consideration of the pK(a) values, charge distribution, and geometry of the respective acid mimics. Several of the compounds have CCK-B binding affinities similar to the parent carboxylic acid 1 (CCK-B, IC50 = 1.7 nM; pK(a) = 5.6) and span a pK(a) range of <1 (sulfonic acid 27) to >9.5 (5-thio-1,2,4-triazole 24). Among the more active compounds synthesized are tricyclo[3.3.1.1(3,7)]dec-2-yl [R-(R*,R*)]-[2-[[2-[[(3-hydroxy-5-isoxazolyl)acetyl]-amino]-2-phenylethyl]amino]-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl]carbamate (15), tricyclo[3.3.1.1(3,7)]dec-2-yl [R-(R*,R*)]-[1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[[2-[(1-oxo-3-sulfopropyl)amino]-2-phenylethyl]amino]-ethyl]carbamate, monosodium salt (27), and tricyclo[3.3.1.1(3,7)]dec-2-yl [R-(R*,R*)]-[1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[[2-1[(1H-1,2,4-triazol-5-ylsulfinyl)acetyl]amino]-2-phenylethyl]amino]ethyl]carbamic acid (34) which have CCK-B binding affinities of IC50 = 2.6,1.3, and 1.7 nM, CCK-A/-B ratios of 650,780, and 550 and pK(a) values of 6.5, <1, and 7.0, respectively.

  DOI：

  10.1021/jm00092a007

文献信息

• Inhibitors of protein tyrosine phosphatase
  申请人：Pharmacia & Upjohn Company

  公开号：US06353023B1

  公开（公告）日：2002-03-05

  The present invention comprises small molecular weight, non-peptidic inhibitors of formula I and II of Protein Tyrosine Phosphatase 1 (PTP1) which are useful for the treatment and/or prevention of Non-Insulin Dependent Diabetes Mellitus (NIDDM).

  本发明涉及小分子量、非肽类的蛋白酪氨酸磷酸酶1（PTP1）的化学式I和II的抑制剂，用于治疗和/或预防非胰岛素依赖型糖尿病（NIDDM）。
• Synthesis, Characterization and In Vitro Evaluation of Novel 5-Ene-thiazolo[3,2-b][1,2,4]triazole-6(5H)-ones as Possible Anticancer Agents
  作者：Serhii Holota、Sergiy Komykhov、Stepan Sysak、Andrzej Gzella、Andriy Cherkas、Roman Lesyk

  DOI：10.3390/molecules26041162

  日期：——

  anticancer properties using the thiazolo[3,2-b][1,2,4]triazole-6-one scaffold. A series of 24 novel thiazolo-[3,2-b][1,2,4]triazole-6-ones with 5-aryl(heteryl)idene- and 5-aminomethylidene-moieties has been synthesized employing three-component and three-stage synthetic protocols. A mixture of Z/E-isomers was obtained in solution for the synthesized 5-aminomethylidene-thiazolo[3,2-b]-[1,2,4]triazole-6-ones

  本文致力于使用噻唑并[3,2- b ][ 1,2,4 ]三唑-6-酮支架寻找具有抗癌特性的药物样分子。采用三组分和三种方法合成了一系列 24 种具有 5-芳基（杂基）亚基和 5-氨基亚甲基-部分的新型噻唑并-[3,2- b ][ 1,2,4 ]三唑-6-酮。 -阶段合成方案。在合成的5-氨基亚甲基-噻唑并[3,2 - b ]-[ 1,2,4 ]三唑-6-酮的溶液中获得Z/E-异构体的混合物。已在 NCI 60 线筛选中研究了这些化合物的抗肿瘤活性。一些化合物在 10 μM 时表现出优异的抗癌特性。衍生物2h和2i对癌细胞系最有效，且不会对正常体细胞 (HEK293) 产生毒性。对合成的化合物进行了初步的 SAR 研究。
• Modification of the N-terminus of peptidomimetic protein tyrosine phosphatase 1B (PTP1B) inhibitors: identification of analogues with cellular activity
  作者：Scott D. Larsen、F.Craig Stevens、Thomas J. Lindberg、Paul M. Bodnar、Theresa J. O'Sullivan、Heinrich J. Schostarez、Barbara J. Palazuk、John E. Bleasdale

  DOI：10.1016/s0960-894x(02)01065-x

  日期：2003.3

  Low molecular weight peptidomimetic compounds based on 0-malonyl tyrosine and 0-carboxymethyl salicylic acid are potent inhibitors of PTP1B. Modifications of the N-terminal Boc-Phe moiety were undertaken in an effort to improve physical chemical properties and to achieve cellular activity. Although Phe ultimately proved to be the optimal N-terminal amino acid, several viable replacements for the Boc group were identified, two of which afforded analogues that were effective at enhancing the insulin-stimulated uptake of 2-deoxyglucose by L6 myocytes. (C) 2003 Elsevier Science Ltd. All rights reserved.
• KNYSH, E. G.;MAZUR, I. A.;ZIMENKOVSKIJ, B. S.;STETS, V. R.;DUNAEV, V. V.;+, XIM.-FARMATS. ZH., 1984, 18, N 11, 1324-1327
  作者：KNYSH, E. G.、MAZUR, I. A.、ZIMENKOVSKIJ, B. S.、STETS, V. R.、DUNAEV, V. V.、+

  DOI：——

  日期：——
• Synthesis and biological activity of 6-ylidenethiazolidino[3,2-c]-1,2,4-triazol-5-ones
  作者：E. G. Knysh、I. A. Mazur、B. S. Zimenkovskii、V. R. Smets、V. V. Dunaev、P. N. Steblyuk

  DOI：10.1007/bf00779899

  日期：1984.11