4-(5-mercapto-1,3,4-thiadiazol-2-yl)phenol | 115249-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(5-mercapto-1,3,4-thiadiazol-2-yl)phenol
• 英文别名: 5-(4-hydroxy-phenyl)-1,3,4-thiadiazole-2-thiol；5-(4-hydroxy-phenyl)-1,3,4-thiazole-2-thiol；5-[4-Hydroxyphenyl]-1,3,4-thiadiazole-2(3H)-thione；5-(4-hydroxyphenyl)-3H-1,3,4-thiadiazole-2-thione
• CAS: 115249-57-5
• 化学式: C₈H₆N₂OS₂
• 分子量: 210.28
• InChiKey: SPCOJHSDAVLPJE-UHFFFAOYSA-N

物化性质

• 沸点：
  365.8±44.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5-mercapto-1,3,4-thiadiazol-2-yl)phenol 、 5(S)-3,4-dibromo-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-2(5H)-furanone 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 水 、 苯 为溶剂， 以66%的产率得到(2S)-4-bromo-3-[[5-(4-hydroxyphenyl)-1,3,4-thiadiazol-2-yl]sulfanyl]-2-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-2H-furan-5-one
  参考文献：
  名称：

  Synthesis of new chiral 2,5-disubstituted 1,3,4-thiadiazoles possessing γ-butenolide moiety and preliminary evaluation of in vitro anticancer activity

  摘要：

  A new series of chiral 1,3,4-thiadiazoles derivatives possessing gamma-substituted butenolide moiety were synthesized and evaluated for in vitro anticancer properties. All the compounds showed good anticancer activities against Hela cell lines. Of ail the studied compounds, compound Sle exhibited the best inhibitory activity with an IC50 of 0-9 mu M. After being treated with 0.1 mu g/mL compound 9e for 24 h, the growth inhibition rate of Hela cell lines was 59.2%. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.023
• 作为产物：
  描述：

  Potassium;4-[(dithiocarboxyamino)carbamothioyl]phenolate 在 水 作用下， 以 甲醇 为溶剂， 反应 168.0h， 以40%的产率得到4-(5-mercapto-1,3,4-thiadiazol-2-yl)phenol
  参考文献：
  名称：

  Studies on novel Cu(II) complexes of 5-(4-hydroxy-phenyl)-1,3,4-thiadiazole-2-thiol and 5-thiophen-2-yl-3H-1,3,4-oxadiazole-2-thione: Synthesis, spectral and structural characterization

  摘要：

  Two new mixed ligand complexes, [Cu(en)(2)](4-hpythol)(2)center dot 2H(2)O (4-hpythol = 5-(4-hydroxy-phenyl)-1,3,4-thiadiazole-2-thiol) (2) and [Cu(en)(2)(5-thot)(2)] (5-thot = 5-thiophen-2-yl-3H-1,3,4-oxadiazole-2-thione (3), have been prepared, containing en as the co-ligand. The starting ligands, potassium salts of thiohydrazide carbodithioate (RCSNHNHCSSK)/hydrazine carbodithioate (RCONHNHCSSK), underwent cyclization during the crystallization or complexation in the presence of ethylenediamine (en) and converted to 5-(4-hydroxy-phenyl)-1,3,4-thiadiazole-2-thiol and 5-thiophen-2-yl-3H-1,3,4-oxadiazole-2-thione, respectively. The metal complexes have been characterized with the aid of elemental analyses. IR, magnetic susceptibility and single crystal X-ray studies. The ligand 4-hpythol and complexes 2 and 3 crystallize in the triclinic and monoclinic systems, space group P 21/n, P (1) over bar and P 21/c, respectively. The ligand is present in the deprotonated thiol form in [Cu(en)(2)](4-hpythol)(2)center dot 2H(2)O (2), where it is ionically bonded through the thiol sulfur atom, while potassium N'-(thiophene-2-carbonyl) hydrazinecarbodithioate after cyclization is present as the thione form in [Cu(en)(2)(5-thot)(2)] (3) and is covalently bonded through the N atom of the resulting oxadiazole-2-thione. The most noteworthy feature of 4-hpythol (1) is its existence in the thiol form in the solid state. Complex 3 show irreversible redox behavior, assignable to a M2+/M3+ one electron transfer. ESR signals were registered for complexes 2 and 3. Both complexes contain extended hydrogen bonding, providing supramolecular frameworks. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.04.025

文献信息

• Synthesis of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as potent antiproliferative agents via a hybrid pharmacophore approach
  作者：Daiki Kaneko、Masayuki Ninomiya、Rina Yoshikawa、Yukari Ono、Amol D. Sonawane、Kaori Tanaka、Atsuyoshi Nishina、Mamoru Koketsu

  DOI：10.1016/j.bioorg.2020.104293

  日期：2020.11

  been shown higher in vitro potency than imiquimod. Besides, triazole, oxadiazole, and thiadiazole rings are privileged building blocks in drug design. A series of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole and [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-thiadiazole derivatives were therefore synthesized by incorporation of these rings into the structure of EAPB0203 and assessed their antiproliferative

  咪喹莫特（1-异丁基-1 H-咪唑并[4,5 - c ]喹啉-4-胺）对某些类型的皮肤癌有效。结构相似的EAPB0203（N-甲基-1-（2-苯乙基）咪唑并[1,2 - a ]喹喔啉-4-胺）的体外药效比咪喹莫特更高。此外，三唑，恶二唑和噻二唑环是药物设计中的重要组成部分。一系列[1,2,4]三唑并[4,3 - a ]喹喔啉-1,3,4-恶二唑和[1,2,4]三唑并[4,3- a因此，通过将这些环并入EAPB0203的结构中来合成]喹喔啉-1,3,4-噻二唑衍生物，并评估它们对多种癌细胞系的抗增殖作用。与咪喹莫特和EAPB0203相比，1,3,4-恶二唑衍生物表现出卓越的功效。我们的发现突出了[1,2,4]三唑并[4,3 - a ]喹喔啉-1,3,4-恶二唑衍生物作为抗癌剂的巨大潜力。
• New potent inhibitors of tyrosinase: Novel clues to binding of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides to the dicopper active site
  作者：Usman Ghani、Nisar Ullah

  DOI：10.1016/j.bmc.2010.04.021

  日期：2010.6.1

  hydrazides were tailored and synthesized as new potent inhibitors of tyrosinase. The rationale for inhibitor design was based on the active site structural evidence from the crystal structures of bacterial tyrosinase and potato catechol oxidase enzymes. Kinetic and active site binding studies suggested mono-dentate binding of thiadiazole, oxadiazole, and triazole rings to the active site dicopper center

  一系列1,3,4-噻二唑-2（3 H）-硫酮，1,3,4-恶二唑-2（3 H）-硫酮，4-氨基-1,2,4-三唑-5（4）H）-硫酮和取代的酰肼被定制并合成为酪氨酸酶的新型有效抑制剂。设计抑制剂的基本原理是基于细菌酪氨酸酶和马铃薯儿茶酚氧化酶的晶体结构的活性位点结构证据。动力学和活性位点结合研究表明，噻二唑，恶二唑和三唑环与酪氨酸酶活性位点双铜中心的单齿结合包括疏水性，有助于有效抑制。动力学图显示了所有25种化合物的混合抑制类型。发现在对酪氨酸酶的高结合亲和力中，三唑环的C3取代和噻二唑/恶二唑环的C5取代起主要作用。
• Cephalosporin derivatives, processes for their preparation and antibacterial agents
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：EP0241901A2

  公开（公告）日：1987-10-21

  l. A compound having the formula: wherein R is a straight chain or branched chain lower alkyl, cyclic lower alkyl, lower alkenyl (except for I-carboxy-l-vinyl), lower alkynyl, aralkyl, phenyl or 2-pyrrolidon-3-yl group which may be substituted, and Q is (wherein R' is a hydrogen atom or an acetyl group, R2 is a hydrogen atom, a carboxyl group or a carboxymethyl group, Y is a sulfur atom or an oxygen atom, Z is a sulfur atom, an oxygen atom or an imino group which may be substituted by a lower alkyl group); or a pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof.

  l. 具有以下式子的化合物： 其中 R 是可被取代的直链或支链低级烷基、环状低级烷基、低级烯基（I-羧基-l-乙烯基除外）、低级炔基、芳基、苯基或 2-吡咯烷-3-基，Q 是（其中 R' 是氢原子或乙酰基，R2 是氢原子、羧基或羧甲基，Y 是硫原子或氧原子，Z 是硫原子、氧原子或可被低级烷基取代的亚氨基）；或其药学上可接受的盐、生理上可水解的酯或溶液。
• 一种含磺酸酯结构的噻二唑酰胺类化合物及其制备方法和应用
  申请人：贵州大学

  公开号：CN117186028A

  公开（公告）日：2023-12-08

  本发明涉及化工技术与农药技术领域，特别是涉及一种含磺酸酯结构的噻二唑酰胺类化合物及其制备方法和应用。本发明以4‑羟基苯甲基酰肼为原料合成一系列含磺酸酯结构的噻二唑酰胺类化合物，所合成的噻二唑酰胺类化合物对农业病虫害中的水稻白叶枯病菌、水稻细条病菌、柑橘溃疡病菌和猕猴桃溃疡病菌具有一定的抑制作用，对桃蚜具有一定的杀虫作用，对小菜蛾有较好的杀虫活性，可用于制备杀小菜蛾药剂。
• US5061794A
  申请人：——

  公开号：US5061794A

  公开（公告）日：1991-10-29