2,5-二甲氧基-硫代苯甲酰胺 | 351065-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,5-二甲氧基-硫代苯甲酰胺
• 英文名称: 2,5-dimethoxybenzothioamide
• 英文别名: 2,5-Dimethoxythiobenzamid；2,5-Dimethoxythiobenzamide；2,5-dimethoxybenzenecarbothioamide
• CAS: 351065-79-7
• 化学式: C₉H₁₁NO₂S
• 分子量: 197.258
• InChiKey: XQBSOMICYVLAMS-UHFFFAOYSA-N

物化性质

• 沸点：
  354.7±52.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  76.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  2,5-二甲氧基-硫代苯甲酰胺 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氯化亚砜 、 nickel(II) chloride hexahydrate 、 乙醇 、 水 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 33.0h， 生成 4‐[(1Z)‐({2‐[2‐(2,5‐dimethoxyphenyl)‐1,3‐thiazol‐5‐yl]ethyl}imino)(phenyl)methyl]benzene‐1,3‐diol
  参考文献：
  名称：

  一种噻唑类衍生物及其合成方法

  摘要：

  本发明属于有机合成技术领域，具体涉及一种噻唑类衍生物及其合成方法，特别是涉及一种噻唑类衍生物(Z)‑4‑((2‑(2‑(2‑(2,5‑二甲氧基苯基)噻唑‑5基)乙基亚氨基)(苯基)甲基)‑1,3‑苯二酚及其合成方法，本发明提供的合成方法为：以2,5‑二甲氧基苯甲酰胺和2‑氯乙酸乙酯为原料，经羰基硫、取代、环化、取代、氯代、氰化、酰胺化、水解以及取代反应九步反应制备了(Z)‑4‑((2‑(2‑(2‑(2,5‑二甲氧基苯基)噻唑‑5基)乙基亚氨基)(苯基)甲基)‑1,3‑苯二酚，为该噻唑类衍生物的合成提供了一种高效合成的方法。

  公开号：

  CN111875557B
• 作为产物：
  描述：

  2,5-二甲氧基苯甲酸 在 劳森试剂 、 ammonium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 10.0h， 生成 2,5-二甲氧基-硫代苯甲酰胺
  参考文献：
  名称：

  3H-1,2,4-Dithiazol-3-one compounds as novel potential affordable antitubercular agents

  摘要：

  Small molecules with oxathiazol-2-one moiety were recently reported as potent inhibitors of Mycobacterium bovis var. bacilli Calmette-Guerin (BCG), among which HT1171 was the most potent and selective proteasome inhibitor. Herein we synthesized a series of novel compounds by bioisosteric replacement of the oxathiazol-2-one ring with 3H-1,2,4-dithiazol-3-one, and also fifteen 1,3,4-oxathiazol-2-one molecules in order for potency comparison and structure-activity relationship elucidation since their antibacterial effects on the virulent strains were not evaluated before. All the compounds were assessed for antitubercular activities on the virulent H37Rv strain by a serial dilution method. Among the tested compounds, 3H-1,2,4-dithiazol-3-one compound 4n was found to be the most active with a lowest MIC90 value of 1 mu g/mL. Furthermore, the cytotoxicities of all the compounds against normal human liver cell line L02 were determined by an MTT method. Compound 4n displayed a lower inhibitory ratio than HT1171 at the concentration of 100 mu M, indicating its better safety profile. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.065

文献信息

• Discovery of novel P2 substituted 4-biaryl proline inhibitors of hepatitis C virus NS3 serine protease
  作者：Murray D. Bailey、Teddy Halmos、Christopher T. Lemke

  DOI：10.1016/j.bmcl.2013.05.046

  日期：2013.8

  Inhibitors of hepatitis C virus NS3 serine protease often incorporate a large P2 moiety to interact with the surface of the enzyme while shielding part of the catalytic triad. This feature is important in many inhibitors in order to have the necessary potency needed for efficacy. In this Letter we explore some new P2 motifs to further exploit this region of the enzyme. In a continuing effort to replace the often found 4-hydroxyproline P2 core found in the majority of inhibitors for this target, various directly attached aryl derivatives were evaluated. Of these, the 2,4-disubstituted thiazole core proved to be the most interesting. SAR around this motif has lead to compounds with K-i's in the high picomolar range and provided cellular potencies in the single digit nM range. (C) 2013 Elsevier Ltd. All rights reserved.
• OXADIAZOLE, THIADIAZOLE AND TRIAZOLE DERIVATIVES AND COMBINATORIAL LIBRARIES THEREOF
  申请人：TREGA BIOSCIENCES, INC.

  公开号：EP1126833A2

  公开（公告）日：2001-08-29
• EP1126833A4
  申请人：——

  公开号：EP1126833A4

  公开（公告）日：2004-09-08
• [EN] OXADIAZOLE, THIADIAZOLE AND TRIAZOLE DERIVATIVES AND COMBINATORIAL LIBRARIES THEREOF<br/>[FR] DERIVES OXADIAZOLE, THIADIAZOLE ET TRIAZOLE ET BIBLIOTHEQUES COMBINATOIRES CONTENANT CES DERIVES
  申请人：TREGA BIOSCIENCES INC

  公开号：WO2000025768A1

  公开（公告）日：2000-05-11

  The present invention relates to novel compounds of formula (I) wherein X1, X2, X3, X4, T, U and V have the meanings provided. The invention further relates to combinatorial libraries containing at least two or more such compounds, and to methods of preparing combinatorial libraries composed of such compounds.
• 3H-1,2,4-Dithiazol-3-one compounds as novel potential affordable antitubercular agents
  作者：Jianzhong Yang、Weiyi Pi、Li Xiong、Wei Ang、Tao Yang、Jun He、Yuanyuan Liu、Ying Chang、Weiwei Ye、Zhenling Wang、Youfu Luo、Yuquan Wei

  DOI：10.1016/j.bmcl.2012.12.065

  日期：2013.3

  Small molecules with oxathiazol-2-one moiety were recently reported as potent inhibitors of Mycobacterium bovis var. bacilli Calmette-Guerin (BCG), among which HT1171 was the most potent and selective proteasome inhibitor. Herein we synthesized a series of novel compounds by bioisosteric replacement of the oxathiazol-2-one ring with 3H-1,2,4-dithiazol-3-one, and also fifteen 1,3,4-oxathiazol-2-one molecules in order for potency comparison and structure-activity relationship elucidation since their antibacterial effects on the virulent strains were not evaluated before. All the compounds were assessed for antitubercular activities on the virulent H37Rv strain by a serial dilution method. Among the tested compounds, 3H-1,2,4-dithiazol-3-one compound 4n was found to be the most active with a lowest MIC90 value of 1 mu g/mL. Furthermore, the cytotoxicities of all the compounds against normal human liver cell line L02 were determined by an MTT method. Compound 4n displayed a lower inhibitory ratio than HT1171 at the concentration of 100 mu M, indicating its better safety profile. (C) 2012 Elsevier Ltd. All rights reserved.