N-(苯甲酰基硫基)苯甲酰胺 | 134861-13-5

• 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: N-(苯甲酰基硫基)苯甲酰胺
• 中文别名: N-（苄硫基）苯甲酰胺
• 英文名称: N-(benzoylthio)benzamide
• 英文别名: H2S Donor 5a；S-benzamido benzenecarbothioate
• CAS: 134861-13-5
• 化学式: C₁₄H₁₁NO₂S
• 分子量: 257.313
• InChiKey: IJYATHJDICJZLJ-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140℃ (dichloromethane hexane )
• 密度：
  1.266±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 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

制备方法与用途

H₂S供体5a是一种由半胱氨酸激活的H₂S供体，在生物系统中发挥着重要作用，是H₂S研究中的一个有用工具。

反应信息

• 作为反应物：
  描述：

  N-(苯甲酰基硫基)苯甲酰胺 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：

  硫代苯甲酸 在 potassium hydroxide 、 hydroxylamine-O-sulfonic acid 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.33h， 生成 N-(苯甲酰基硫基)苯甲酰胺
  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
• 作为试剂：
  描述：

  L-半胱氨酸 在 N-(苯甲酰基硫基)苯甲酰胺 作用下， 以 甲醇 为溶剂， 以95%的产率得到L-胱氨酸
  参考文献：
  名称：

  Cysteine-Activated Hydrogen Sulfide (H₂S) Donors

  摘要：

  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.

  DOI：

  10.1021/ja1085723

文献信息

• 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。
• Hydrogen sulfide releasing polymer compounds
  申请人：CROMA-PHARMA GESELLSCHAFT M.B.H.

  公开号：US11331338B2

  公开（公告）日：2022-05-17

  The invention provides a hydrogen sulfide releasing polymer compound having a polysaccharide backbone, wherein the compound has at least two substructures, and wherein said substructures are capable of releasing hydrogen sulfide by thiol activation as well as uses thereof. Additionally, a method of treatment and prevention of a skin condition, an ocular disease or osteoarthritis is provided.

  本发明提供了一种具有多糖骨架的硫化氢释放聚合物化合物，其中该化合物具有至少两个亚结构，所述亚结构能够通过硫醇活化释放硫化氢及其用途。此外，还提供了一种治疗和预防皮肤病、眼疾或骨关节炎的方法。
• 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.
• HYDROGEN SULFIDE RELEASING POLYMER COMPOUNDS
  申请人：Croma-Pharma Gesellschaft m.b.H.

  公开号：EP3534886A1

  公开（公告）日：2019-09-11
• METHODS FOR PROTECTING HAIR FOLLICLES
  申请人：Applied Biology, Inc.

  公开号：US20210030787A1

  公开（公告）日：2021-02-04

  Disclosed herein are compositions including a topical agent that may be used to reduce and/or inhibit the effects of chemotherapy and/or radiotherapy, which can include reducing and/or inhibiting the effects of hair loss and/or hair shedding due to chemotherapy and/or radiotherapy. The topical agent can be hydrogen sulfide, a hydrogen sulfide donor, or a substrate for a hydrogen sulfide producing enzyme such as sulfanegen. Some embodiments of the composition can include the topical agent combined with an agent to promote vasoconstriction or the topical agent combined with an agent to modulate deposition, mode of action, and/or metabolism of a chemotherapeutic agent and/or a reactive oxygen species agent. Embodiments can be used for improving the outcome of a hair transplant surgery by optimizing a holding solution to stabilize hair follicle grafts. In yet another embodiment, a system for realizing hydrogen sulfide slowly into a holding solution is described.