4-amino-3-(2,5-dimethoxyphenyl)-1H-1,2,4-triazole-5-thione | 1003849-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-amino-3-(2,5-dimethoxyphenyl)-1H-1,2,4-triazole-5-thione
• CAS: 1003849-84-0
• 化学式: C₁₀H₁₂N₄O₂S
• mdl: MFCD16247819
• 分子量: 252.297
• InChiKey: QVZLTCHWUVERCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-3-(2,5-dimethoxyphenyl)-1H-1,2,4-triazole-5-thione 、 2-溴-2,4-二甲氧基苯乙酮 以 乙醇 为溶剂， 反应 4.0h， 生成 triazolothiadiazine, 9F
  参考文献：
  名称：

  鉴定用于选择性抑制 PDE4 的有效新化学型。

  摘要：

  制备并分析了一系列取代的 3,6-二苯基-7H-[1,2,4] 三唑并 [3,4-b][1,3,4] 噻二嗪作为磷酸二酯酶 4 (PDE4) 的抑制剂。介绍了合成、构效关系以及针对相关磷酸二酯酶同种型的高效类似物的选择性。

  DOI：

  10.1016/j.bmcl.2008.01.028
• 作为产物：
  描述：

  potassium 2-(2,5-dimethoxybenzoyl)hydrazine-1-carbodithioate 在 一水合肼 作用下， 以 水 为溶剂， 反应 0.75h， 生成 4-amino-3-(2,5-dimethoxyphenyl)-1H-1,2,4-triazole-5-thione
  参考文献：
  名称：

  鉴定用于选择性抑制 PDE4 的有效新化学型。

  摘要：

  制备并分析了一系列取代的 3,6-二苯基-7H-[1,2,4] 三唑并 [3,4-b][1,3,4] 噻二嗪作为磷酸二酯酶 4 (PDE4) 的抑制剂。介绍了合成、构效关系以及针对相关磷酸二酯酶同种型的高效类似物的选择性。

  DOI：

  10.1016/j.bmcl.2008.01.028

文献信息

• [EN] PHOSPHODIESTERASE INHIBITORS<br/>[FR] INHIBITEURS DE PHOSPHODIESTÉRASE
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2009089027A1

  公开（公告）日：2009-07-16

  The invention relates to compounds of formula I useful for inhibiting phosphodiesterase-4.

  这项发明涉及到公式I的化合物，用于抑制磷酸二酯酶-4。
• 3-Aryl-6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20080045514A1

  公开（公告）日：2008-02-21

  Disclosed are 3-aryl-6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and analogs thereof, represented by the Formula I: wherein Ar 1 , Q 2 , R 1 , R 2 , dashed line and X are defined herein. The present invention relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及一种由公式I表示的3-芳基-6-芳基-7H-[1,2,4]三唑并[3,4-b][1,3,4]噻二嗪及其类似物，其中Ar1，Q2，R1，R2，虚线和X的定义如下。本发明发现具有公式I的化合物是caspases的激活剂和凋亡诱导剂。因此，本发明的caspases激活剂和凋亡诱导剂可用于诱导在各种临床病况中出现的异常细胞的无控制增长和扩散的细胞死亡。
• Exploration and optimization of substituted triazolothiadiazines and triazolopyridazines as PDE4 inhibitors
  作者：Amanda P. Skoumbourdis、Christopher A. LeClair、Eduard Stefan、Adrian G. Turjanski、William Maguire、Steven A. Titus、Ruili Huang、Douglas S. Auld、James Inglese、Christopher P. Austin、Stephen W. Michnick、Menghang Xia、Craig J. Thomas

  DOI：10.1016/j.bmcl.2009.01.057

  日期：2009.7

  An expansion of structure-activity studies on a series of substituted 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine PDE4 inhibitors and the introduction of a related [1,2,4]triazolo[4,3-b]pyridazine based inhibitor of PDE4 is presented. The development of SAR included strategic incorporation of known substituents on the critical catachol diether moiety of the 6-phenyl appendage on each heterocyclic core. From these studies, (R)-3-(2,5-dimethoxyphenyl)-6-(4-methoxy-3-(tetrahydrofuran-3-yloxy)phenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine (10) and (R)-3-(2,5-dimethoxyphenyl)-6-(4-methoxy-3-(tetrahydrofuran-3-yloxy)phenyl)-[1,2,4]triazolo[4,3-b]pyridazine (18) were identified as highly potent PDE4A inhibitors. Each of these analogues was submitted across a panel of 21 PDE family members and was shown to be highly selective for PDE4 isoforms (PDE4A, PDE4B, PDE4C, PDE4D). Both 10 and 18 were then evaluated in divergent cell-based assays to assess their relevant use as probes of PDE4 activity. Finally, docking studies with selective ligands (including 10 and 18) were undertaken to better understand this chemotypes ability to bind and inhibit PDE4 selectively. (C) 2009 Published by Elsevier Ltd.
• A Novel 7<i>H</i>-[1,2,4]Triazolo[3,4-<i>b</i>]thiadiazine-based Cystic Fibrosis Transmembrane Conductance Regulator Potentiator Directed toward Treatment of Cystic Fibrosis
  作者：Andras Rab、Xun Yang、William F. Tracy、Jeong S. Hong、Disha Joshi、Candela Manfredi、Sadhana S. Ponnaluri、Alexander A. Kolykhalov、Min Qui、Haian Fu、Yuhong Du、Huw M. L. Davies、Eric J. Sorscher

  DOI：10.1021/acsmedchemlett.3c00155

  日期：2023.10.12
• 3-ARYL-6-ARYL-7H-[1,2,4]TRIAZOLO[3,4-b][1,3,4]THIADIAZINES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF
  申请人：Cytovia, Inc.

  公开号：EP2046336A2

  公开（公告）日：2009-04-15