2-amino-5-(4-hydroxy-3-methoxyphenyl)-1,3,4 thiadiazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-amino-5-(4-hydroxy-3-methoxyphenyl)-1,3,4 thiadiazole
• 英文别名: 4-(5-Amino-1,3,4-thiadiazol-2-yl)-2-methoxyphenol
• 化学式: C₉H₉N₃O₂S
• 分子量: 223.255
• InChiKey: BSPCBZUBIMXXLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-5-(4-hydroxy-3-methoxyphenyl)-1,3,4 thiadiazole 在 吡啶 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 N-[5-(4-hydroxy-3-methoxyphenyl)-1,3,4-thiadiazol-2-yl]nonamide
  参考文献：
  名称：

  Design and synthesis of conformationally restricted capsaicin analogues based in the 1, 3, 4-thiadiazole heterocycle reveal a novel family of transient receptor potential vanilloid 1 (TRPV1) antagonists

  摘要：

  4-hydroxy-3-methoxybenzaldehyde was used as starting material to obtain a number of I, 3, 4-thiadiazole alkylamide derivatives. The pharmacological properties of these conformationally restricted capsaicin analogues were evaluated on HEK-293T cells transiently expressing TRPV1 receptor. By means of a highthroughput calcium imaging assay we find that 1, 3, 4-thiadiazoles (compounds 8-15) act as potent antagonists of the capsaicin receptor, inhibiting both, the capsaicin- and temperature-dependent activation. Docking studies suggested a different binding orientation on the vanilloid binding site when compared with capsaicin analogues, such as 5-iodononivamide. Overall, our studies suggest that 1, 3, 4-thiadiazoles interact with capsaicin's binding region of the receptor, although using a different set of interactions within the vanilloid binding pocket. (C) 2013 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2013.05.001
• 作为产物：
  描述：

  乙酰香兰素 在 甲醇 、 iron(III) chloride 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 2-amino-5-(4-hydroxy-3-methoxyphenyl)-1,3,4 thiadiazole
  参考文献：
  名称：

  EP2924028

  摘要：

  公开号：

文献信息

• TRPV-1 RECEPTOR ANTAGONIST COMPOUND DERIVED FROM 1,3,4-THIADIAZOLE ALKYLAMIDES AND CHALCONES
  申请人：UNIVERSIDAD DE CONCEPCION

  公开号：US20160039778A1

  公开（公告）日：2016-02-11

  This technology encompasses compounds derived from 1,3,4-thiadiazole alkylamides and chalcone, which inhibit the activation of the TRPV-1 receptor using capsaicin and temperature. Also disclosed is the use of these compounds in the treatment of diseases with TRPV-1 overexpression, such as chronic pain.

  这项技术包括从1,3,4-噻二唑烷基酰胺和查尔酮中提取的化合物，这些化合物通过使用辣椒素和温度抑制TRPV-1受体的激活。此外，还披露了这些化合物在治疗TRPV-1过度表达的疾病，如慢性疼痛方面的用途。
• 1,3,4-Thiadiazole: A Promising Pharmacophore
  作者：Nidhi Chaudhary、Ranjana Dubey、Tilak Ram、Hament Panwar

  DOI：10.13005/ojc/390222

  日期：2023.4.30

  Active pharmaceutical ingredients (A.P.I.) are made up of various heteroatomic moieties. Numerous heterocycle scaffolds are regarded as crucial structures. More frequently, presence of various heteroatoms viz. nitrogen, sulphur, halogens, and oxygen atoms at different position in 5- or 6-membered rings contributed them as valued source of therapeutic profiles in literature of medicinal chemistry. In the current study, numerous novels 1,3,4-thiadiazole derivatives were created using a multi-step synthetic method. These thiadiazole derivatives comprised 2-amino-5-phenyl-1,3,4-thiadiazole, piperazine, acetophenones, and quinolin-5-ol. 1H-NMR, IR, Mass, and elemental analyses were used to describe these thiadiazole derivatives (C, H, N). The antibacterial, antifungal, and insecticidal efficacy of thiadiazole 4a-4i mimics was investigated.

  活性药物成分（A.P.I.）由各种杂原子分子组成。许多杂环支架被认为是重要的结构。更常见的是，在 5 或 6 元环的不同位置上存在各种杂原子，即氮、硫、卤素和氧原子，这使它们成为药物化学文献中治疗概况的重要来源。在目前的研究中，我们采用多步合成法创造了许多新型 1,3,4-噻二唑衍生物。这些噻二唑衍生物包括 2-氨基-5-苯基-1,3,4-噻二唑、哌嗪、苯乙酮和喹啉-5-醇。利用 1H-NMR、IR、Mass 和元素分析来描述这些噻二唑衍生物（C、H、N）。研究了噻二唑 4a-4i 模拟物的抗菌、抗真菌和杀虫功效。
• EP2924028
  申请人：——

  公开号：——

  公开（公告）日：——
• Design and synthesis of conformationally restricted capsaicin analogues based in the 1, 3, 4-thiadiazole heterocycle reveal a novel family of transient receptor potential vanilloid 1 (TRPV1) antagonists
  作者：Carolyne Lespay Rebolledo、Pamela Sotelo-Hitschfeld、Sebastián Brauchi、Miguel Zárraga Olavarría

  DOI：10.1016/j.ejmech.2013.05.001

  日期：2013.8

  4-hydroxy-3-methoxybenzaldehyde was used as starting material to obtain a number of I, 3, 4-thiadiazole alkylamide derivatives. The pharmacological properties of these conformationally restricted capsaicin analogues were evaluated on HEK-293T cells transiently expressing TRPV1 receptor. By means of a highthroughput calcium imaging assay we find that 1, 3, 4-thiadiazoles (compounds 8-15) act as potent antagonists of the capsaicin receptor, inhibiting both, the capsaicin- and temperature-dependent activation. Docking studies suggested a different binding orientation on the vanilloid binding site when compared with capsaicin analogues, such as 5-iodononivamide. Overall, our studies suggest that 1, 3, 4-thiadiazoles interact with capsaicin's binding region of the receptor, although using a different set of interactions within the vanilloid binding pocket. (C) 2013 Published by Elsevier Masson SAS.