S-benzamido 3-chlorobenzenecarbothioate | 1259992-56-7

• 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: S-benzamido 3-chlorobenzenecarbothioate
• CAS: 1259992-56-7
• 化学式: C₁₄H₁₀ClNO₂S
• 分子量: 291.758
• InChiKey: QNTPIMLKNSMMHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-benzamido 3-chlorobenzenecarbothioate 在 乙二胺四乙酸 、 谷胱甘肽 作用下， 以 aq. phosphate buffer 为溶剂， 生成 硫化氢
  参考文献：
  名称：

  Controlled chemical release of hydrogen sulfide

  摘要：

  提供了以下公式的药剂：其中R1和R2独立变化，可以是酰基、磺酰基、磷酰基、烷基、取代烷基、卤素、芳基、芳基烷基、取代芳基、杂芳基、烯基、取代烯基、炔基、取代炔基、环烷基、杂环烷基或杂原子；而R3是H或者是一个包括R2的环结构的成员；还提供了以下公式的药剂：其中R1、R2和R3独立变化，且：R1=OH、OR′、NHR′、NR′R″（其中R′、R″=烷基、芳基、杂芳基等）；R2=酰基、烷基、芳基、磺酰基等；R3=烷基、芳基、取代芳基、杂芳基等；而R4和R5是（独立的）H、甲基或烷基、取代烷基、芳基、取代芳基等。提供了使用这些药剂治疗心血管疾病、中风、休克、缺氧引起的损伤、男性勃起功能障碍和阿尔茨海默病的方法。

  公开号：

  US09096504B2
• 作为产物：
  描述：

  3-chlorothiobenzoic 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 3-chlorobenzenecarbothioate
  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

文献信息

• Controlled chemical release of hydrogen sulfide
  申请人：Xian Ming

  公开号：US09096504B2

  公开（公告）日：2015-08-04

  Agents of formula: where R1 and R2 vary independently and are acyl, sulfonyl, phosphoryl, alkyl, substituted alkyl, halogen, aryl, arylalkyl, substituted aryl, heteroaryl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, heterocycle, or heteroatoms; and R3 is H or a member of a ring structure which includes R2, are provided; as are agents of formula: where R1, R2 and R3 vary independently and: R1=OH, OR′, NHR′, NR′R″ (with R′ R″=alkyl, aryl, heteroaryl, etc); R2=acyl, alkyl, aryl, sulfonyl, etc; R3=alkyl, aryl, substituted aryl, heteroaryl, etc; and R4 and R5 are (independently) H, methyl or alkyl, substituted alkyl, aryl, substituted aryl, etc. Methods of using the agents to treat e.g. cardiovascular disease, stroke, shock, injuries caused by hypoxia, male erectile dysfunction, and Alzheimer's are provided.

  提供了以下公式的药剂：其中R1和R2独立变化，可以是酰基、磺酰基、磷酰基、烷基、取代烷基、卤素、芳基、芳基烷基、取代芳基、杂芳基、烯基、取代烯基、炔基、取代炔基、环烷基、杂环烷基或杂原子；而R3是H或者是一个包括R2的环结构的成员；还提供了以下公式的药剂：其中R1、R2和R3独立变化，且：R1=OH、OR′、NHR′、NR′R″（其中R′、R″=烷基、芳基、杂芳基等）；R2=酰基、烷基、芳基、磺酰基等；R3=烷基、芳基、取代芳基、杂芳基等；而R4和R5是（独立的）H、甲基或烷基、取代烷基、芳基、取代芳基等。提供了使用这些药剂治疗心血管疾病、中风、休克、缺氧引起的损伤、男性勃起功能障碍和阿尔茨海默病的方法。
• CONTROLLED CHEMICAL RELEASE OF HYDROGEN SULFIDE
  申请人：Xian Ming

  公开号：US20130253051A1

  公开（公告）日：2013-09-26

  Agents of formula: where R1 and R2 vary independently and are acyl, sulfonyl, phosphoryl, alkyl, substituted alkyl, halogen, aryl, arylalkyl, substituted aryl, heteroaryl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, heterocycle, or heteroatoms; and R3 is H or a member of a ring structure which includes R2, are provided; as are agents of formula: where R1, R2 and R3 vary independently and: R1=OH, OR′, NHR′, NR′R″ (with R′ R″=alkyl, aryl, heteroaryl, etc); R 2 =acyl, alkyl, aryl, sulfonyl, etc; R3=alkyl, aryl, substituted aryl, heteroaryl, etc; and R4 and R5 are (independently) H, methyl or alkyl, substituted alkyl, aryl, substituted aryl, etc. Methods of using the agents to treat e.g. cardiovascular disease, stroke, shock, injuries caused by hypoxia, male erectile dysfunction, and Alzheimer's are provided.

  提供了公式代理人：其中R1和R2分别变化且独立，并且为酰基，磺酰基，磷酰基，烷基，取代烷基，卤素，芳基，芳基烷基，取代芳基，杂环芳基，烯基，取代烯基，炔基，取代炔基，环烷基，杂环，或杂原子; 而R3为H或包括R2的环结构的成员; 提供了公式代理人：其中R1，R2和R3独立变化且：R1 = OH，OR′，NHR′，NR′R″（其中R′ R″ = 烷基，芳基，杂环芳基等）; R2 = 酰基，烷基，芳基，磺酰基等; R3 = 烷基，芳基，取代芳基，杂环芳基等; 而R4和R5为（独立的）H，甲基或烷基，取代烷基，芳基，取代芳基等。提供了使用这些代理人治疗心血管疾病，中风，休克，缺氧引起的损伤，男性勃起功能障碍和阿尔茨海默病的方法。
• US9096504B2
  申请人：——

  公开号：US9096504B2

  公开（公告）日：2015-08-04
• [EN] CONTROLLED CHEMICAL RELEASE OF HYDROGEN SULFIDE<br/>[FR] LIBÉRATION CHIMIQUE CONTRÔLÉE DE SULFURE D'HYDROGÈNE
  申请人：UNIV WASHINGTON STATE RES FDN

  公开号：WO2012075242A2

  公开（公告）日：2012-06-07

  Agents of formula: where R1 and R2 vary independently and are acyl, sulfonyl, phosphoryl, alkyl, substituted alkyl, halogen, aryl, arylalkyl, substituted aryl, heteroaryl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, heterocycle, or heteroatoms; and R3 is H or a member of a ring structure which includes R2, are provided; as are agents of formula: where R1, R2 and R3 vary independently and: R1 = OH, OR', NHR', NR'R" (with R' R" = alkyl, aryl, heteroaryl, etc); R2 = acyl, alkyl, aryl, sulfonyl, etc; R3 = alkyl, aryl, substituted aryl, heteroaryl, etc; and R4 and R5 are (independently) H, methyl or alkyl, substituted alkyl, aryl, substituted aryl, etc. Methods of using the agents to treat e.g. cardiovascular disease, stroke, shock, injuries caused by hypoxia, male erectile dysfunction, and Alzheimer's are provided.
• 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.