(+)-cis-3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one hydrochloride | 158511-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (+)-cis-3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one hydrochloride
• 英文别名: SM 12502 hydrochloride；SM 10661 hydrochloride；(2R,5S)-3,5-Dimethyl-2-pyridin-3-yl-1,3-thiazolidin-4-one;hydrochloride
• CAS: 158511-47-8
• 化学式: C₁₀H₁₂N₂OS*ClH
• 分子量: 244.745
• InChiKey: CXHDSLQCNYLQND-XQRIHRDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-cis-3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one hydrochloride 在 rat liver flavin monooxygenase 1 氧气 、 硫代苯甲酰胺 作用下， 反应 72.0h， 生成 (1R,2R,5R)-3,5-Dimethyl-1-oxo-2-pyridin-3-yl-1λ⁴-thiazolidin-4-one; hydrochloride
  参考文献：
  名称：

  S-oxidation of (+)-cis-3,5-dimethyl-2-(3-pyridyl)-thiazolidin-4-one hydrochloride by rat hepatic flavin-containing monooxygenase 1 expressed in yeast

  摘要：

  1. Rat hepatic flavin-containing monooxygenase 1 (FMO1) expressed in yeast catalyzed the S-oxidation of (+)-cis-3,5-dimethyl-2-(3-pyridyl)thiazolidin hydrochloride (SM-12502) in vitro.2. S-oxidation was inhibited by 1-(1-naphthyl)-2-thiourea and thiobenzamide, known inhibitors of FMO, but was not enhanced by n-octylamine, a known enhancer of FMO.3. The rate of S-oxide formation from SM-12502 was about four-fold lower than that from (+/-)-trans-3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one hydrochloride (SM-9979) and enantioselectivity and diastereoselectivity of the S-oxidation reaction were observed.4. The ability of the recombinant yeast to produce the S-oxide from Sm-12502 was maintained for long periods and exemplifies the recombinant yeast as a bioreactor to produce a large amount of the S-oxide.

  DOI：

  10.3109/00498259509061917
• 作为产物：
  描述：

  (R)-thiolactic acid 、 (E)-n-(吡啶-3-基亚甲基)甲胺 以50的产率得到(+)-cis-3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one hydrochloride
  参考文献：
  名称：

  Thiazolidin-4-one derivatives and acid addition salts thereof useful for

  摘要：

  以下是由下列通式（I）表示的噻唑烷-4-酮衍生物及其酸加成盐 ##STR1## 其中： R.sup.1和R.sup.2相同或不同，且每个都表示（i）由通式--A--R.sup.4表示的残基，其中A表示单键，C.sub.1-C.sub.8烷基，C.sub.2-C.sub.8烯基或C.sub.2-C.sub.8炔基，而R.sup.4表示氢，C.sub.1-C.sub.12烷基，C.sub.2-C.sub.8烯基，C.sub.3-C.sub.8环烷基或C.sub.1-C.sub.6卤代烷基；或（ii）由通式表示的残基##STR2## 其中，B表示单键或C.sub.1-C.sub.6烷基，R.sup.5表示氢，C.sub.1-C.sub.6烷基，C.sub.2-C.sub.8烯基，C.sub.3-C.sub.8环烷基，取代的硅烷基或取代或未取代的芳基，n和n'各自表示2到4的整数，m表示1到3的整数，m'表示0到2的整数；R.sup.3表示氢，C.sub.1-C.sub.2烷基，烯丙基，2-丙炔基或（c）通式--F--R.sup.9，其中，F表示C.sub.2-C.sub.6烷基，而R.sup.9表示含氮杂环芳基残基或由通式表示的氨基团##STR3## （R.sup.10表示氢，C.sub.2-C.sub.4烷基或C.sub.1-C.sub.4烷酰基，而R.sup.11表示氢或C.sub.1-C.sub.4烷基，或R.sup.10与R.sup.11结合形成5-到7-成员的环状氨基团，该环状氨基团可选地包含其他杂原子。这些化合物具有选择性的PAF拮抗活性，非常有用作为预防和治疗PAF诱导的疾病，例如各种炎症，过敏性疾病，循环系统疾病和胃肠疾病的药物。

  公开号：

  US05106860A1

文献信息

• Thiazolidin-4-one derivatives and acid addition salts thereof useful for
  申请人：Sumitomo Chemical Company, Limited

  公开号：US05106860A1

  公开（公告）日：1992-04-21

  Thiazolidin-4-one derivative represented by the following general formula (I) and acid addition salts thereof ##STR1## wherein; R.sup.1 and R.sup.2 are the same or different and denote each (i) a residue represented by the general formula --A--R.sup.4 wherein, A denotes a single bond, C.sub.1 -C.sub.8 alkylene, C.sub.2 -C.sub.8 alkenylene, or C.sub.2 -C.sub.8 alkynylene and R.sup.4 denotes hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, or C.sub.1 -C.sub.6 haloalkyl,or (ii) a residue represented by the general formula ##STR2## wherein, B denotes a single bond or C.sub.1 -C.sub.6 alkylene, R.sup.5 denotes hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, substituted silyl, or substituted or unsubstituted aryl, n and n' denote each an integer of 2 to 4, m denotes an integer of 1 to 3, and m' denotes an integer of 0 to 2; R.sup.3 denotes hydrogen, C.sub.1 -C.sub.2 alkyl, allyl, 2-propynyl, or (c) the general formula --F--R.sup.9 wherein, F denotes C.sub.2 -C.sub.6 alkylene and R.sup.9 denotes a nitrogen-containing heterocyclic aromatic residue or an amino group represented by the general formula ##STR3## (R.sup.10 denotes hydrogen, C.sub.2 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkanoyl and R.sup.11 denotes hydrogen or C.sub.1 -C.sub.4 alkyl or R.sup.10 in combination with R.sup.11 denotes a 5- to 7-membered cyclic amino group which optionally contains other hetero atoms. Having selective PAF-antagonistic activities, these compounds are very useful as preventive and curative agents for PAF-induced diseases, for example, various kinds of inflammation, allergic diseases, circulatory diseases, and gastro-intestinal diseases.

  以下是由下列通式（I）表示的噻唑烷-4-酮衍生物及其酸加成盐 ##STR1## 其中： R.sup.1和R.sup.2相同或不同，且每个都表示（i）由通式--A--R.sup.4表示的残基，其中A表示单键，C.sub.1-C.sub.8烷基，C.sub.2-C.sub.8烯基或C.sub.2-C.sub.8炔基，而R.sup.4表示氢，C.sub.1-C.sub.12烷基，C.sub.2-C.sub.8烯基，C.sub.3-C.sub.8环烷基或C.sub.1-C.sub.6卤代烷基；或（ii）由通式表示的残基##STR2## 其中，B表示单键或C.sub.1-C.sub.6烷基，R.sup.5表示氢，C.sub.1-C.sub.6烷基，C.sub.2-C.sub.8烯基，C.sub.3-C.sub.8环烷基，取代的硅烷基或取代或未取代的芳基，n和n'各自表示2到4的整数，m表示1到3的整数，m'表示0到2的整数；R.sup.3表示氢，C.sub.1-C.sub.2烷基，烯丙基，2-丙炔基或（c）通式--F--R.sup.9，其中，F表示C.sub.2-C.sub.6烷基，而R.sup.9表示含氮杂环芳基残基或由通式表示的氨基团##STR3## （R.sup.10表示氢，C.sub.2-C.sub.4烷基或C.sub.1-C.sub.4烷酰基，而R.sup.11表示氢或C.sub.1-C.sub.4烷基，或R.sup.10与R.sup.11结合形成5-到7-成员的环状氨基团，该环状氨基团可选地包含其他杂原子。这些化合物具有选择性的PAF拮抗活性，非常有用作为预防和治疗PAF诱导的疾病，例如各种炎症，过敏性疾病，循环系统疾病和胃肠疾病的药物。
• EP1893993A4
  申请人：——

  公开号：EP1893993A4

  公开（公告）日：2009-05-13
• CRYSTAL OF A CYTOCHROME-LIGAND COMPLEX AND METHODS OF USE
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：EP1893993A2

  公开（公告）日：2008-03-05
• JPH07304689A
  申请人：——

  公开号：JPH07304689A

  公开（公告）日：1995-11-21
• JPH09187300A
  申请人：——

  公开号：JPH09187300A

  公开（公告）日：1997-07-22