(R)-2-acetylamino-3-(benzoylthio)propionic acid | 62147-00-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-acetylamino-3-(benzoylthio)propionic acid
• 英文别名: (2R)-2-acetamido-3-benzoylsulfanylpropanoic acid
• CAS: 62147-00-6
• 化学式: C₁₂H₁₃NO₄S
• 分子量: 267.306
• InChiKey: UEVPAYOBBXAHJC-JTQLQIEISA-N

物化性质

• 沸点：
  511.4±50.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氨乙硝酸 、 (R)-2-acetylamino-3-(benzoylthio)propionic acid 在 焦碳酸二乙酯 作用下， 生成 (2R)-N-(2-Nitrooxyethyl)-2-acetylamino-3-benzoylthiopropanamide
  参考文献：
  名称：

  Synthesis and collateral dilator activity of nitroxyalkylamides having direct or latent sulfhydryl moieties

  摘要：

  To develop an orally active, long-acting nitrate that does not induce tolerance, nitroxyalkyl compounds were prepared and their activities evaluated by the use of carotid collaterals in anesthetized dogs. A compound having a favorable pharmacological profile, that is, long-lasting collateral vasodilatation and little hypotension, and lack of nitrate tolerance, was chosen for further evaluation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00199-9
• 作为产物：
  描述：

  苯甲酰氯 生成 (R)-2-acetylamino-3-(benzoylthio)propionic acid
  参考文献：
  名称：

  EP903346

  摘要：

  公开号：

文献信息

• Cobalt assisted cleavage of SS bonds and a base-free synthesis of mercapturic acids
  作者：Shantanu Chowdhury、Sujit Roy

  DOI：10.1016/s0040-4039(97)00268-2

  日期：1997.3

  Base free transformation of PhSSPh to sulfides, PhSR (R= alkyl, benzyl, allyl, acyl) and N-acetyl-L-cystine to mercapturic acids [AcNHCH(COOH)CH2SR, R= alkyl, benzyl, allyl, acyl] have been achieved using Zn/cat. CoCl2/organic halide in MeCN at room temperature.

  PhSSPh的无碱转化为硫化物，PhSR（R =烷基，苄基，烯丙基，酰基）和N-乙酰基-L-胱氨酸转化为巯基酸[AcNHCH（COOH）CH 2 SR，R =烷基，苄基，烯丙基，酰基]使用锌/催化剂已经实现。室温下在MeCN中的CoCl 2 /有机卤化物。
• Direct Observation of Acyl Nitroso Compounds in Aqueous Solution and the Kinetics of Their Reactions with Amines, Thiols, and Hydroxamic Acids
  作者：Eric Maimon、Ana Lerner、Amram Samuni、Sara Goldstein

  DOI：10.1021/acs.jpca.8b06672

  日期：2018.9.6

  Acyl nitroso compounds or nitrosocarhonyls (RC(O)N═O) are reactive short-lived electrophiles, and their hydrolysis and reactions with nucleophiles produce HNO. Previously, direct detection of acyl nitroso species in nonaqueous media has been provided by time-resolved infrared spectroscopy demonstrating that its half-life is about 1 ms. In the present study hydroxamic acids (RC(O)NHOH) are oxidized

  酰基亚硝基化合物或亚硝基羰基化合物（RC（O）N = O）是反应性短寿命的亲电试剂，它​​们的水解和与亲核试剂的反应会生成HNO。以前，时间分辨红外光谱法可直接检测非水介质中的酰基亚硝基，证明其半衰期约为1毫秒。在本研究中，异羟肟酸（RC（O）NHOH）在缓冲水溶液（pH 5.9-10.2）中被电化学氧化，产生瞬态物质，其特征在于它们在314-330 nm处具有最大吸收。这些瞬态物质通过一级反应分解，主要产生HNO和相应的羧酸，因此归因于RC（O）N = O。RC（O）N = O在水溶液中足够长的半衰期首次允许研究其与各种亲核试剂的反应动力学，这表明亲核反应性遵循硫醇盐>异羟肟酸酯>胺的顺序。CH的金属螯合物3 C（O）NHOH以Cu II > Zn II > Ni II > Co II的功效顺序催化CH 3 C（O）N = O的水解，其中在不存在异羟肟酸酯的情况下，只有Cu II催化水解
• AMINO ACID DERIVATIVE
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0641769A1

  公开（公告）日：1995-03-08

  Constitution: an amino acid derivative represented by the general formula (I): R¹NH-CH(R²)-CONH-A-ONO₂ and a pharmacologically acceptable salt thereof, wherein R¹ represents hydrogen, C₁-C₇ alkanoyl, C₁-C₆ alkoxycarbonyl, C₆-C₁₀ arylcarbonyl, C₇-C₁₃ aralkylcarbonyl, C₇-C₁₃ aralkyloxycarbonyl, or 5- or 6-membered heteroarylcarbonyl; R² represents substituted C₁-C₆ alkyl; and A represents C₂-C₅ alkylene. Effect: this compound is excellent in a collateral vessel dilator activity and an antianginal activity, and hence useful as an antianginal drug.

  构成：通式(I)代表的氨基酸衍生物：R¹NH-CH(R²)-CONH-A-ONO₂ 及其药理学上可接受的盐，其中 R¹ 代表氢、C₁-C₇ 烷酰基C₁-C₆烷氧基羰基、C₆-C₁₀芳基羰基、C₇-C₁₃ 芳基羰基、C₇-C₁₃ 芳基氧基羰基或 5 或 6 元杂芳基羰基；R² 代表取代的 C₁-C₆ 烷基；以及 A 代表 C₂-C₅ 亚烷基。功效：该化合物具有良好的扩张侧支血管活性和抗心绞痛活性，因此可用作抗心绞痛药物。
• SYDNONE IMINE DERIVATIVES
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0903346A1

  公开（公告）日：1999-03-24

  Compounds represented by the following general formula (1) or pharmaceutically acceptable salts thereof: [wherein Z represents -A-X-R1, a heterocycle or cycloalkyl; A represents a methylene group; X represents a sulfur atom; R1 represents a benzoyl group; R2 represents - N(R3)R4 (wherein R3 represents a methyl group; and R4 represents an optionally substituted alkyl group, etc.); or a group represented by the following general formula (2): wherein R5 and R6 represent each a hydrogen atom; and Y represents a group represented by the following general formula (3): (wherein R4 is as defined above)}]. Because of having vasodilative effect, myocardial protective effect, antiplatelet aggregation effect, etc., the compounds represented by the above general formula (1) or pharmaceutically acceptable salts thereof are useful as drugs such as therapeutic medicines for angina pectoris.

  由以下通式（1）代表的化合物或其药学上可接受的盐类： [其中 Z 代表-A-X-R1、杂环或环烷基；A 代表亚甲基；X 代表硫原子；R1 代表苯甲酰基；R2 代表-N(R3)R4(其中 R3 代表甲基；R4 代表任选取代的烷基等)；或下 列通式(2)所代表的基团： 其中 R5 和 R6 各代表一个氢原子；Y 代表由下式通式 (3) 所代表的基团： (其中 R4 如上定义）}]。 由于具有血管扩张作用、心肌保护作用、抗血小板聚集作用等，上述通式（1）所代表的化合物或其药学上可接受的盐类可用作药物，如心绞痛的治疗药物。
• Portelli; Renzi; Cervato, Farmaco, Edizione Scientifica, 1976, vol. 31, # 11, p. 767 - 775
  作者：Portelli、Renzi、Cervato、Frigeni

  DOI：——

  日期：——