methyl (2-chloroethanesulfinyl)acetate | 113207-10-6

• 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: methyl (2-chloroethanesulfinyl)acetate
• 英文别名: methyl [(2-chloroethyl)sulfinyl]acetate；Methyl2-(2-chloroethylsulfinyl)acetat；methyl 2-(2-chloroethylsulfinyl)acetate
• CAS: 113207-10-6
• 化学式: C₅H₉ClO₃S
• 分子量: 184.644
• InChiKey: QCASOZFALSMYCA-UHFFFAOYSA-N

物化性质

• 沸点：
  334.0±27.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2-chloroethanesulfinyl)acetate 、 DL-高半胱氨酸 在 sodium carbonate 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 49.0h， 生成 2-Amino-4-(2-carboxymethanesulfinyl-ethylsulfanyl)-butyric acid
  参考文献：
  名称：

  S-Alkylated Homocysteine Derivatives:  New Inhibitors of Human Betaine-Homocysteine S-Methyltransferase

  摘要：

  A series of S-alkylated derivatives of homocysteine were synthesized and characterized as inhibitors of human recombinant betaine-homocysteine S-methyltransferase ( BHMT). Some of these compounds inhibit BHMT with IC50 values in the nanomolar range. BHMT is very sensitive to the structure of substituents on the sulfur atom of homocysteine. The S-carboxybutyl and S-carboxypentyl derivatives make the most potent inhibitors, and an additional sulfur atom in the alkyl chain is well tolerated. The respective ( R, S)-5-( 3-amino-3-carboxy-propylsulfanyl)-pentanoic, ( R, S)-6-( 3-amino-3-carboxy-propylsulfanyl)-hexanoic, and ( R, S)2-amino-4-(2-carboxymethylsulfanyl- ethylsulfanyl)-butyric acids are very potent inhibitors and are the strongest ever reported. We determined that ( R, S)-5-( 3-amino-3-carboxy-propylsulfanyl)-pentanoic acid displays competitive inhibition with respect to betaine binding with a K-i(app) of 12 nM. Some of these compounds are currently being tested in mice to study the influence of BHMT on the metabolism of sulfur amino acids in vivo.

  DOI：

  10.1021/jm050885v
• 作为产物：
  描述：

  2-(2-氯乙基巯基)乙酸甲酯 在 盐酸 、 双氧水 作用下， 以56%的产率得到methyl (2-chloroethanesulfinyl)acetate
  参考文献：
  名称：

  S-Alkylated Homocysteine Derivatives:  New Inhibitors of Human Betaine-Homocysteine S-Methyltransferase

  摘要：

  A series of S-alkylated derivatives of homocysteine were synthesized and characterized as inhibitors of human recombinant betaine-homocysteine S-methyltransferase ( BHMT). Some of these compounds inhibit BHMT with IC50 values in the nanomolar range. BHMT is very sensitive to the structure of substituents on the sulfur atom of homocysteine. The S-carboxybutyl and S-carboxypentyl derivatives make the most potent inhibitors, and an additional sulfur atom in the alkyl chain is well tolerated. The respective ( R, S)-5-( 3-amino-3-carboxy-propylsulfanyl)-pentanoic, ( R, S)-6-( 3-amino-3-carboxy-propylsulfanyl)-hexanoic, and ( R, S)2-amino-4-(2-carboxymethylsulfanyl- ethylsulfanyl)-butyric acids are very potent inhibitors and are the strongest ever reported. We determined that ( R, S)-5-( 3-amino-3-carboxy-propylsulfanyl)-pentanoic acid displays competitive inhibition with respect to betaine binding with a K-i(app) of 12 nM. Some of these compounds are currently being tested in mice to study the influence of BHMT on the metabolism of sulfur amino acids in vivo.

  DOI：

  10.1021/jm050885v

文献信息

• Phenolic thioethers as inhibitors of 5-lipoxygenase
  申请人：G. D. Searle & Co.

  公开号：US04711903A1

  公开（公告）日：1987-12-08

  The compounds of the present invention comprise substituted phenolic thioethers represented by the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are the same or different and independently represent tert-alkyl or phenyl; A represents methylene or methylene substituted by alkyl, dialkyl or hydroxy, provided that when A includes hydroxymethylene, the hydroxymethylene group is not adjacent to a heteroatom; B represents sulfur, sulfoxide, sulfone, oxygen, --NH-- or nitrogen substituted by alkyl, phenyl, benzyl, substituted phenyl or substituted benzyl; C represents methylene or methylene substituted by alkyl; R.sub.3 represents CO.sub.2 H, CO.sub.2 -alkyl or a tetrazole group; m is 0 or 1, n is 2, 3 or 4 and p is 1, 2 or 3; amd the pharmaceutically acceptable salts thereof. The compounds of the present invention are specific inhibitors of 5-lipoxygenase and, therefore, are useful in the treatment of local and systemic inflammation, allergy and hypersensitivity reactions and other disorders in which agents formed in the 5-lipoxygenase metabolic pathway are involved.

  本发明的化合物包括由以下式表示的取代酚硫醚：##STR1##其中：R.sub.1和R.sub.2相同或不同且独立地表示叔烷基或苯基；A表示亚甲基或被烷基、二烷基或羟基取代的亚甲基，但当A包括羟甲基时，羟甲基基团不与杂原子相邻；B表示硫、亚硫氧、砜、氧、--NH--或被烷基、苯基、苄基、取代苯基或取代苄基取代的氮；C表示亚甲基或被烷基取代的亚甲基；R.sub.3表示CO.sub.2 H、CO.sub.2 -烷基或四唑基团；m为0或1，n为2、3或4，p为1、2或3；以及其药学上可接受的盐。本发明的化合物是5-脂氧合酶的特异性抑制剂，因此在治疗局部和全身炎症、过敏和过敏反应以及其他涉及5-脂氧合酶代谢途径中形成的药物的紊乱方面具有用处。
• Novel phenolic thioethers as inhibitors of 5-lipoxygenase
  申请人：G. D. Searle & Co.

  公开号：US04755524A1

  公开（公告）日：1988-07-05

  The compounds of the present invention comprise substituted phenolic thioethers represented by the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are the same or different and independently represent tert-alkyl or phenyl; A represents methylene or methylene substituted by alkyl, dialkyl or hydroxy, provided that when A includes hydroxymethylene, the hydroxymethylene group is not adjacent to a heteroatom; B represents sulfur, sulfoxide, sulfone, oxygen, --NH-- or nitrogen substituted by alkyl, phenyl, benzyl, substituted phenyl or substituted benzyl; C represents methylene or methylene substituted by alkyl; R.sub.3 represents CO.sub.2 H, CO.sub.2 -alkyl or a tetrazole group; m is 0 or 1, n is 2, 3 or 4 and p is 1, 2 or 3; and the pharmaceutically acceptable salts thereof. The compounds of the present invention are specific inhibitors of 5-lipoxygenase and, therefore, are useful in the treatment of local and systemic inflammation, allergy and hypersensitivity reactions and other disorders in which agents formed in the 5-lipoxygenase metabolic pathway are involved.

  本发明的化合物包括由以下式子表示的取代苯基硫醚：##STR1## 其中：R.sub.1和R.sub.2相同或不同，分别表示叔丁基或苯基；A表示亚甲基或被烷基、二烷基或羟基取代的亚甲基，但当A包括羟甲基时，羟甲基基团不与杂原子相邻；B表示硫、亚砜、砜、氧、--NH--或被烷基、苯基、苄基、取代苯基或取代苄基取代的氮；C表示亚甲基或被烷基取代的亚甲基；R.sub.3表示CO.sub.2 H、CO.sub.2 -烷基或四唑基团；m为0或1，n为2、3或4，p为1、2或3；以及其药学上可接受的盐。本发明的化合物是5-脂氧合酶的特异性抑制剂，因此，在治疗局部和全身炎症、过敏和超敏反应以及其他涉及5-脂氧合酶代谢途径中形成的药物时具有用途。
• <b><i>S</i></b>-Alkylated Homocysteine Derivatives:  New Inhibitors of Human Betaine-Homocysteine <i>S</i>-Methyltransferase
  作者：Jiri Jiracek、Michaela Collinsova、Ivan Rosenberg、Milos Budesinsky、Eva Protivinska、Hana Netusilova、Timothy A. Garrow

  DOI：10.1021/jm050885v

  日期：2006.6.1

  A series of S-alkylated derivatives of homocysteine were synthesized and characterized as inhibitors of human recombinant betaine-homocysteine S-methyltransferase ( BHMT). Some of these compounds inhibit BHMT with IC50 values in the nanomolar range. BHMT is very sensitive to the structure of substituents on the sulfur atom of homocysteine. The S-carboxybutyl and S-carboxypentyl derivatives make the most potent inhibitors, and an additional sulfur atom in the alkyl chain is well tolerated. The respective ( R, S)-5-( 3-amino-3-carboxy-propylsulfanyl)-pentanoic, ( R, S)-6-( 3-amino-3-carboxy-propylsulfanyl)-hexanoic, and ( R, S)2-amino-4-(2-carboxymethylsulfanyl- ethylsulfanyl)-butyric acids are very potent inhibitors and are the strongest ever reported. We determined that ( R, S)-5-( 3-amino-3-carboxy-propylsulfanyl)-pentanoic acid displays competitive inhibition with respect to betaine binding with a K-i(app) of 12 nM. Some of these compounds are currently being tested in mice to study the influence of BHMT on the metabolism of sulfur amino acids in vivo.