4-(dimethylamino)thiobenzoic acid

• 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: 4-(dimethylamino)thiobenzoic acid
• 英文别名: 4-Dimethylamino-thiobenzoesaeure；4-(dimethylamino)benzenecarbothioic S-acid
• 化学式: C₉H₁₁NOS
• 分子量: 181.258
• InChiKey: DTXBFNZDMFXQSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(dimethylamino)thiobenzoic acid 在 potassium hydroxide 、 hydroxylamine-O-sulfonic acid 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.08h， 生成 S-benzamido 4-(dimethylamino)benzenecarbothioate
  参考文献：
  名称：

  Design, Synthesis, and Cardioprotective Effects of N-Mercapto-Based Hydrogen Sulfide Donors

  摘要：

  Hydrogen sulfide (H2S) is a signaling molecule which plays regulatory roles in many physiological and/or pathological processes. Therefore, regulation of H2S levels could have great potential therapeutic value. In this work, we report the design, synthesis, and evaluation of a class of N-mercapto (N-SH)-based H2S donors. Thirty-three donors were synthesized and tested. Our results indicated that controllable H2S release from these donors could be achieved upon structural modifications. Selected donors (NSHD-1, NSHD-2, and NSHD-6) were tested in cellular models of oxidative damage and showed significant cytoprotective effects. Moreover, NSHD-1 and NSHD-2 were also found to exhibit potent protective effects in a murine model of myocardial ischemia reperfusion (MI/R) injury.

  DOI：

  10.1021/acs.jmedchem.5b01033
• 作为产物：
  描述：

  硫光气 、 N,N-二甲基苯胺 生成 4-(dimethylamino)thiobenzoic acid
  参考文献：
  名称：

  Rivier; Richard, Helvetica Chimica Acta, 1925, vol. 8, p. 499

  摘要：

  DOI：

文献信息

• Aminolysis of <i>O</i>-Aryl Thionobenzoates: Amine Basicity Combines with Modulation of the Nature of Substituents in the Leaving Group and Thionobenzoate Moiety to Control the Reaction Mechanism
  作者：Ik-Hwan Um、So-Jeong Hwang、Sora Yoon、Sang-Eun Jeon、Sun-Kun Bae

  DOI：10.1021/jo801539w

  日期：2008.10.3

  nucleophile and nucleofuge, that is, the reaction proceeds through T(+/-) when the leaving aryloxide is less basic than the attacking amine, but through T(+/-) and T(-) when the leaving group is more basic than the amine. However, the reaction mechanism is not influenced by the electronic nature of the substituent X in the nonleaving group. The Hammett plot for the reactions of 2a-f with benzylamine is

  动力学研究表明，OY取代的苯基硫代苯甲酸酯（1a-f）和O-4-硝基苯基X取代的硫代苯甲酸酯（2a-f）在80 mol％H2O / 20 mol％DMSO中在25.0 +/- 0.1度下氨解C.通过亲核试剂和亲核试剂之间的碱性差异，通过一种或两种中间体（即两性离子四面体中间体T（+/-）及其去质子化形式T（-））进行反应，即反应通过当离去的芳基氧化物比攻击性胺的碱性差时，T（+/-），但当离去的基团比胺的碱性更高时，则通过T（+/-）和T（-）。然而，反应机理不受非离去基团中取代基X的电子性质的影响。2a-f与苄胺反应的哈米特图由两条相交的直线组成，可以将其解释为速率确定步骤（RDS）中的更改。然而，相同反应的汤川-日野图表现出极好的线性相关性，表明非线性哈米特图不是由于RDS的变化，而是由于电子之间的共振相互作用而使基质的基态稳定而引起的。 -供体取代基X和硫代羰基部分。
• Cysteine-Activated Hydrogen Sulfide (H₂S) Donors
  作者：Yu Zhao、Hua Wang、Ming Xian

  DOI：10.1021/ja1085723

  日期：2011.1.12

  H2S, the newly discovered gasotransmitter, plays important roles in biological systems. However, the research on H2S has been hindered by the lack of controllable H2S donors that could mimic the slow and continuous H2S generation process in vivo. Herein we report a series of cysteine-activated H2S donors. Structural modifications of these molecules can regulate the rates of H2S generation. These compounds can be useful tools in H2S research.
• DE37730
  申请人：——

  公开号：——

  公开（公告）日：——
• Design, Synthesis, and Cardioprotective Effects of <i>N</i>-Mercapto-Based Hydrogen Sulfide Donors
  作者：Yu Zhao、Chuntao Yang、Chelsea Organ、Zhen Li、Shashi Bhushan、Hiro Otsuka、Armando Pacheco、Jianming Kang、Hector C. Aguilar、David J. Lefer、Ming Xian

  DOI：10.1021/acs.jmedchem.5b01033

  日期：2015.9.24

  Hydrogen sulfide (H2S) is a signaling molecule which plays regulatory roles in many physiological and/or pathological processes. Therefore, regulation of H2S levels could have great potential therapeutic value. In this work, we report the design, synthesis, and evaluation of a class of N-mercapto (N-SH)-based H2S donors. Thirty-three donors were synthesized and tested. Our results indicated that controllable H2S release from these donors could be achieved upon structural modifications. Selected donors (NSHD-1, NSHD-2, and NSHD-6) were tested in cellular models of oxidative damage and showed significant cytoprotective effects. Moreover, NSHD-1 and NSHD-2 were also found to exhibit potent protective effects in a murine model of myocardial ischemia reperfusion (MI/R) injury.
• Rivier; Richard, Helvetica Chimica Acta, 1925, vol. 8, p. 499
  作者：Rivier、Richard

  DOI：——

  日期：——