(2S,3S)-3-甲基-2-(3-氧代-1,2-苯并噻唑-2(3H)-基)戊酸 | 177785-47-6

• 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
• 中文名称: (2S,3S)-3-甲基-2-(3-氧代-1,2-苯并噻唑-2(3H)-基)戊酸
• 中文别名: (2S,3S)-3-甲基-2-(3-羰基-2,3-二氢-1,2-苯并异噻唑-2-YL)缬草酸
• 英文名称: (2S,3S)-3-methyl-2-(3-oxo-3H-benzo[d]isothiazol-2-yl)pentanoic acid
• 英文别名: [S-(R*,R*)]-3-Methyl-2-(3-oxo-3H-benzo[d] isothiazol-2-yl)pentanoic acid；(2S,3S)-3-methyl-2-(3-oxo-1,2-benzothiazol-2-yl)pentanoic acid
• CAS: 177785-47-6
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: FUSYFEXGXRDJNB-KWQFWETISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-乙酰-L-半胱氨酸 、 (2S,3S)-3-甲基-2-(3-氧代-1,2-苯并噻唑-2(3H)-基)戊酸 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 以84%的产率得到
  参考文献：
  名称：

  苯并异噻唑酮的开环反应。不对称二硫化物的新途径

  摘要：

  通过采用涉及开环的反应制备了一系列不对称的二硫键，硫醇对1，2-苯并噻唑-3-酮进行了亲核攻击。苯并异噻唑酮依次通过亚硫基硫代碳酸酯上的酰胺的分子内闭环来制备。合成了亚砜基酯作为制备混合二硫化物的中间体，但苯并异噻唑酮的开环是自发发生的。最初认为混合二硫化物是由亚硫基酯形成的，但苯并异噻唑酮的分离和逐步反应为反应机理提供了证据。

  DOI：

  10.1002/jhet.5570340515
• 作为产物：
  描述：

  2,2-二硫二苯甲酰氯 在 N-甲基吗啉 、 溴 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 39.0h， 生成 (2S,3S)-3-甲基-2-(3-氧代-1,2-苯并噻唑-2(3H)-基)戊酸
  参考文献：
  名称：

  Biophysical Characterization of Zinc Ejection from HIV Nucleocapsid Protein by Anti-HIV 2,2‘-Dithiobis[benzamides] and Benzisothiazolones

  摘要：

  HIV nucleocapsid protein (NCp7) has been suggested as a possible target for 2,2'-dithiobis[benzamide] and benzisothiazolone agents that inhibit viral replication in infected cells (Rice et al. Science 1995, 270, 1194-1197). The solution behavior of these compounds and the mechanistic events leading to removal of Zn from HIV nucleocapsid protein in vitro has been studied by electrospray ionization mass spectrometry, 500 MHz one- and two-dimensional nuclear magnetic resonance spectroscopy, and circular dichroism spectroscopy. We demonstrate that (1) Zn ejection is accompanied by formation of covalent complexes formed between the 2,2'-dithiobis[benzamide] monomers and Cys residues of Zn-depleted NCp7, (2) the rate of Zn ejection is faster for the C-terminal Zn finger and slower for the N-terminal finger, (3) Zn ejection results in a loss of structural integrity of the NCp7 protein, and (4) there is no appreciable interaction between a nonreactive iso stere of the lead 2,2'-dithiobis[benzamide] and NCp7 in buffered aqueous solution. These findings are discussed in terms of the mechanism of action of Zn ejection by aromatic 2,2'-dithiobis[benzamides].

  DOI：

  10.1021/jm960253w

文献信息

• Development and Pilot-Scale Demonstration of a Process for Inhibitors of the HIV Nucleocapsid Protein, NCp7
  作者：Phillip J. Fiore、Timothy P. Puls、Jonathan C. Walker

  DOI：10.1021/op9701191

  日期：1998.5.1

  A manufacturing-process to prepare two antiretroviral agents that denature the HIV-1 nucleocapsid protein (NCp7) has been developed and demonstrated on a pilot scale. 2,2'-Dithiobis-(benzoyl chloride) (4), prepared from commercially available 2,2'-dithiobis(benzoic acid) (3), was coupled directly with L-isoleucine to give the potential anti-HIV compound [S-(R*,R*)]- 2-[2-[[2-[(1-carboxy-2-methylbutyl)carbamoyl]phenyl]dithio]benzoyl]amino}-3-methylpentanoic acid (2) thereby eliminating the alpha-amino acid protection and deprotection steps used in the original synthesis. Compound 2 was oxidized by bromine to a second potential anti-HIV compound [S-(R*,R*)]-3-methyl-2-(3-oxo-3H-benzo[d]isothiazol-2-yl) pentanoic acid (1). The intermediacy of the hydrobromide salt of 1 provided an effective purity control in the production of the pharmaceutical agent. Cost, operational, safety, environmental, and equipment considerations were taken into account during the course of development.
• Org. Process Res. Deve. 1998, 2, 151-156
  作者：

  DOI：——

  日期：——
• ARYLTHIO COMPOUNDS AS ANTIBACTERIAL AND ANTIVIRAL AGENTS
  申请人：Warner-Lambert Company LLC

  公开号：EP0775110B1

  公开（公告）日：2005-10-05
• ISOTHIAZOLONES
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0828488A1

  公开（公告）日：1998-03-18
• METHOD OF MAKING (S-(R*,R*))-3-METHYL-2-(3-OXO-3H-BENZO(D)ISOTHIAZOL-2-YL)PENTANOIC ACID AND (S-(R*,R*)), L-2-(2-(2-(1-CARBOXY-2-METHYLBUTYLCARBAMOYL)PHENYLDISULFONYL)BENZOYL-AMINO)-3-METHYLPENTANOIC ACID
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0874835A1

  公开（公告）日：1998-11-04