N-isopropyl-2-mercaptobenzamide | 99075-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-isopropyl-2-mercaptobenzamide
• 英文别名: 2-mercapto-benzoic acid isopropylamide；2-Mercapto-benzoesaeure-isopropylamid；N-propan-2-yl-2-sulfanylbenzamide
• CAS: 99075-15-7
• 化学式: C₁₀H₁₃NOS
• mdl: MFCD24388761
• 分子量: 195.285
• InChiKey: JQSJHMPAFHSPJX-UHFFFAOYSA-N

物化性质

• 熔点：
  97-101 °C(Solv: water, 50% (7732-18-5); ethanol (64-17-5))
• 沸点：
  341.2±25.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-isopropyl-2-mercaptobenzamide 在 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到2-isopropyl-1,2-benzisothiazolin-3-one
  参考文献：
  名称：

  通过脱氢 NS 键形成电化学合成苯并异噻唑-3(2H)-酮

  摘要：

  在此，我们报告了一种从 2-巯基苯甲酰胺合成苯并异噻唑-3(2H)-酮的电化学方法。电化学反应通过分子内 N H/S H 偶联环化反应进行，生成 H 2作为无害副产物。此外，该方法反应时间短，条件温和，底物范围广，无需使用金属催化剂和外源性氧化剂。2009 Elsevier Ltd. 版权所有。

  DOI：

  10.1016/j.tetlet.2021.153323
• 作为产物：
  描述：

  2,2'-dithio-bis(N-isopropyl)benzamide 在 溶剂黄146 、 锌 作用下， 生成 N-isopropyl-2-mercaptobenzamide
  参考文献：
  名称：

  Plasticizing natural and synthetic elastomers by incorporation of n-isopropyl thiosalicylamide

  摘要：

  公开号：

  US02603617A1

文献信息

• A Copper‐Catalyzed, pH‐Neutral Construction of High‐Enantiopurity Peptidyl Ketones from Peptidic <i>S</i> ‐Acylthiosalicylamides in Air at Room Temperature
  作者：Lanny S. Liebeskind、Hao Yang、Hao Li

  DOI：10.1002/anie.200804524

  日期：2009.2.9

  A copper‐catalyzed transformation of peptidic thiol esters and boronic acids gives peptidyl ketones and takes place in DMF or DMF/H2O at room temperature in air (see scheme). This aerobic reaction only occurs at a thiol ester group capable of coordinating to Cu through its appendage on the sulfur center and is not hampered by racemization of the reactants or products.

  肽硫羟酸酯和硼酸的铜催化转化产生肽基酮，并在室温空气中的 DMF 或 DMF/H 2 O 中发生（参见方案）。这种需氧反应仅发生在能够通过硫中心上的附属物与Cu配位的硫羟酸酯基团处，并且不受反应物或产物的外消旋作用的阻碍。
• Exploring the Structural Requirements for Inhibition of the Ubiquitin E3 Ligase Breast Cancer Associated Protein 2 (BCA2) as a Treatment for Breast Cancer
  作者：Ghali Brahemi、Fathima R. Kona、Annalisa Fiasella、Daniela Buac、Jitka Soukupová、Andrea Brancale、Angelika M. Burger、Andrew D. Westwell

  DOI：10.1021/jm901757t

  日期：2010.4.8

  The zinc-ejecting aldehyde dehydrogenase (A LDH) inhibitory drug disulfiram (DS F) was found to be a breast cancer-associated protein 2 (BCA2) inhibitor with potent antitumor activity. We herein describe our work in the synthesis and evaluation of new series of zinc-affinic molecules to explore the structural requirements for selective BCA2-inhibitory antitumor activity. An N(C=S)S-S motif was found to be required, based on selective activity in BCA2-expressing breast cancer cell lines and against recombinant BCA2 protein. Notably, the DSF analogs (3a and 3c) and dithio(peroxo)thioate compounds (5d and 5f) were found to have potent activity (submicromolar IC(50)) in BCA2 positive MCF-7 and T47D cells but were inactive (IC(50)> 10 mu M) in BCA2 negative M DA-MB-231 breast cancer cells and the normal breast epithelial cell line MCF10A. Testing in the isogenic BCA2 +ve M DA-MB-231/ER cell line restored antitumor activity for compounds that were inactive in the BCA2 -ve MDA-MB-231 cell line. In contrast, structurally related dithiocarbamates and benzisothiazolones (lacking the disulfide bond) were all inactive. Compounds 5d and 5f were additionally found to lack ALDH-inhibitory activity, suggestive of selective E3 ligase-inhibitory activity and worthy of further development.