3-(2-ethylthioethyl)-2-imino-6-trifluoromethylbenzothiazoline | 130569-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 3-(2-ethylthioethyl)-2-imino-6-trifluoromethylbenzothiazoline
• 英文别名: 2-Imino-3-(2-ethylthioethyl)-6-trifluoromethylbenzothiazoline；3-(2-ethylsulfanylethyl)-6-(trifluoromethyl)-1,3-benzothiazol-2-imine
• CAS: 130569-71-0
• 化学式: C₁₂H₁₃F₃N₂S₂
• 分子量: 306.376
• InChiKey: JMUKIWYPXBITBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  77.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2-ethylthioethyl)-2-imino-6-trifluoromethylbenzothiazoline 在 间氯过氧苯甲酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 2-imino-3-(2-ethylsulphinylethyl)-6-trifluoromethylbenzothiazoline
  参考文献：
  名称：

  Riluzole Series. Synthesis and in Vivo “Antiglutamate” Activity of 6-Substituted-2-benzothiazolamines and 3-Substituted-2-imino-benzothiazolines

  摘要：

  Two series of analogues of riluzole, a blocker of excitatory amino acid mediated neurotransmission, have been synthesized: monosubstituted 2-benzothiazolamines and 3-substituted derivatives. Of all the compounds prepared in the first series, only 2-benzothiazolamines bearing alkyl, polyfluoroalkyl, or polyfluoroalkoxy substituents in the 6-position showed potent anticonvulsant activity against administration of glutamic acid in rats. The most active compounds displaying in vivo "antiglutamate" activity were the 6-OCF3 (riluzole), 6-OCF2CF3, 6-CF3, and 6-CF2CF3 substituted derivatives with ED50 values between 2.5 and 3.2 mg/kg i.p. Among the second series of variously substituted benzothiazolines, compounds as active as riluzole or up to 3 times more potent were identified in two series: benzothiazolines bearing a beta-dialkylaminoethyl moiety and compounds with an alkylthioalkyl chain and their corresponding sulfoxides and sulfones. The most potent derivatives were 2-imino-3-(2-methylthio)- and 2-imino-3-(2-methylsulfinyl)-ethyl-6-trifluoromethoxybenzothiazlines (61 and 64, ED50 = 10 and 1.1 mg/kg i.p., respectively). In addition, intraperitoneal administration of some of the best benzothiazolines protected mice from mortality produced by hypobaric hypoxia.

  DOI：

  10.1021/jm980202u
• 作为产物：
  描述：

  对三氟甲基苯胺 在 溴 、 溶剂黄146 作用下， 以 丁酮 为溶剂， 反应 45.0h， 生成 3-(2-ethylthioethyl)-2-imino-6-trifluoromethylbenzothiazoline
  参考文献：
  名称：

  Riluzole Series. Synthesis and in Vivo “Antiglutamate” Activity of 6-Substituted-2-benzothiazolamines and 3-Substituted-2-imino-benzothiazolines

  摘要：

  Two series of analogues of riluzole, a blocker of excitatory amino acid mediated neurotransmission, have been synthesized: monosubstituted 2-benzothiazolamines and 3-substituted derivatives. Of all the compounds prepared in the first series, only 2-benzothiazolamines bearing alkyl, polyfluoroalkyl, or polyfluoroalkoxy substituents in the 6-position showed potent anticonvulsant activity against administration of glutamic acid in rats. The most active compounds displaying in vivo "antiglutamate" activity were the 6-OCF3 (riluzole), 6-OCF2CF3, 6-CF3, and 6-CF2CF3 substituted derivatives with ED50 values between 2.5 and 3.2 mg/kg i.p. Among the second series of variously substituted benzothiazolines, compounds as active as riluzole or up to 3 times more potent were identified in two series: benzothiazolines bearing a beta-dialkylaminoethyl moiety and compounds with an alkylthioalkyl chain and their corresponding sulfoxides and sulfones. The most potent derivatives were 2-imino-3-(2-methylthio)- and 2-imino-3-(2-methylsulfinyl)-ethyl-6-trifluoromethoxybenzothiazlines (61 and 64, ED50 = 10 and 1.1 mg/kg i.p., respectively). In addition, intraperitoneal administration of some of the best benzothiazolines protected mice from mortality produced by hypobaric hypoxia.

  DOI：

  10.1021/jm980202u

文献信息

• 2-iminobenzothiazoline derivatives, their preparation and pharmaceutical
  申请人：Rhone-Poulenc Sante

  公开号：US05008280A1

  公开（公告）日：1991-04-16

  Compounds of the formula: ##STR1## in which - R.sub.1 denotes a polyfluoroalkoxy or polyfluoroalkyl radical, and - R.sub.2 denotes either a chain --CH.sub.2 --(CH(R.sub.4)).sub.n --R.sub.3, in which R.sub.3 denotes a dialkylamino, piperidino, 1-pyrrolidinyl, mercapto, acylthio, alkylthio, alkylsulphinyl or alkylsulphonyl radical, R.sub.4 denotes a hydrogen atom or an alkyl radical and n is equal to 0 or 1, or a residue of formula: ##STR2## the said alkyl and alkoxy radicals and portions containing 1 to 4 carbon atoms each in a straight or branched chain and said the acyl portions containing 2 to 4 carbon atoms each, and the salts of these compounds, are useful in the treatment of diseases in which glutamate is implicated.

  化合物的公式为：##STR1## 其中 - R.sub.1表示多氟烷氧基或多氟烷基基团，而 - R.sub.2则表示链 -CH.sub.2--(CH(R.sub.4)).sub.n--R.sub.3，其中R.sub.3表示二烷基氨基，哌啶基，1-吡咯烷基，巯基，酰硫基，烷基硫基，烷基磺酰基基团，R.sub.4表示氢原子或烷基基团，n等于0或1，或者为公式的残基：##STR2## 所述的烷基和烷氧基基团以及含有1至4个碳原子的直链或支链部分，以及含有2至4个碳原子的酰基部分和这些化合物的盐，在涉及谷氨酸的疾病治疗中是有用的。
• APPLICATION DE 2-IMINOBENZOTHIAZOLINES DANS LE TRAITEMENT DU PARKINSON ET DES SYNDROMES PARKINSONIENS
  申请人：RHONE-POULENC RORER S.A.

  公开号：EP0863756A1

  公开（公告）日：1998-09-16
• DERIVES DE 3,4-DIHYDRO 1,2,4]THIADIAZINO 3,4-b]BENZOTHIAZOLE, LEUR PREPARATION ET LES MEDICAMENTS LES CONTENANT
  申请人：RHONE-POULENC RORER S.A.

  公开号：EP0876378A1

  公开（公告）日：1998-11-11
• US5008280A
  申请人：——

  公开号：US5008280A

  公开（公告）日：1991-04-16
• [EN] 3,4-DIHYDRO[1,2,4]THIADIAZINO[3,4-b]BENZOTHIAZOLE DERIVATIVES, PREPARATION THEREOF AND DRUGS CONTAINING SAME<br/>[FR] DERIVES DE 3,4-DIHYDRO[1,2,4]THIADIAZINO[3,4-b]BENZOTHIAZOLE, LEUR PREPARATION ET LES MEDICAMENTS LES CONTENANT
  申请人：RHONE-POULENC RORER S.A.

  公开号：WO1997020850A1

  公开（公告）日：1997-06-12

  (EN) Compounds of formula (I), wherein R is a polyfluoroalkyl radical, R1 is an alkyl radical and Hal is a halogen atom, are disclosed. The compounds of formula (I) are useful for treating Parkinson's disease and parkinsonian syndromes.(FR) Composés de formule (I) dans laquelle R représente un radical polyfluoroalkyle, R1 représente un radical alkyle et Hal représente un atome d'halogène. Les composés de formule (I) sont utiles pour le traitement de la maladie de Parkinson et des syndromes parkinsoniens.