(4aRS,5SR,9bRS)-2-ethyl-7-methyl-2,3,4,4a,5,9b-hexahydro-5-(4-carbomethoxyphenyl)-1H-indeno<1,2-c>pyridine hydrochloride | 162490-13-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4aRS,5SR,9bRS)-2-ethyl-7-methyl-2,3,4,4a,5,9b-hexahydro-5-(4-carbomethoxyphenyl)-1H-indeno<1,2-c>pyridine hydrochloride
• 英文别名: (4aRS, 5SR, 9bRS)5-(4-caboxymethoxyphenyl)-2-ethyl-2,3,4,4a,5,9b-hexahydro-7-methyl-1H-indeno[1,2-c]pyridine hydrochloride；RTI-4587-056；methyl 4-[(4aR,5S,9bR)-2-ethyl-7-methyl-1,3,4,4a,5,9b-hexahydroindeno[1,2-c]pyridin-5-yl]benzoate;hydrochloride
• CAS: 162490-13-3
• 化学式: C₂₃H₂₇NO₂*ClH
• 分子量: 385.934
• InChiKey: AMBJNRAZKHBFDL-PQYKPJTCSA-N

反应信息

• 作为产物：
  描述：

  甲醇 、 4-((4aR,9S,9aR)-3-Ethyl-7-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluoren-9-yl)-benzoic acid; hydrochloride 在 氯化亚砜 作用下， 反应 68.0h， 以2.65 g的产率得到(4aRS,5SR,9bRS)-2-ethyl-7-methyl-2,3,4,4a,5,9b-hexahydro-5-(4-carbomethoxyphenyl)-1H-indeno<1,2-c>pyridine hydrochloride
  参考文献：
  名称：

  Structure-Activity Studies of 2,3,4,4a,5,9b-Hexahydroindeno[1,2-c]pyridines as Antispermatogenic Agents for Male Contraception

  摘要：

  Analogs of (4aRS,5SR,9bRS)-2-ethyl-2,3,4,4a,5,9b-hexahydro-7-methyl-5-p-tolyl-1H-indeno[1,2-c]pyridine (Sandoz 20-438, 10a; R(1) = ethyl, R(2) = R(3) = methyl, R(4) = H) have been synthesized and tested in mice for their ability to reduce testes weight and disrupt spermatogenesis. The activity was strongly dependent on stereoisomerism and chirality, consistent with a mechanism of action involving interaction with a specific macromolecule. It was affected by changes in the nitrogen substituent and most strikingly by changes in the p-substituent of the 5-aryl ring. A hydrogen, fluorine, hydroxy, or methoxy substituent led to loss of activity, whereas methyl (Sandoz 20-438, 10a), carboxylate (RTI-4587-054, 10k; R(1) = ethyl, R(2) = methyl, R(3) = COOH, R(4) = H), ester (RTI-4587-056, 12b; R(1) = ethyl, R(2) = methyl, R(3) = COOMe, R(4) = H), formyl (RTI-4587-030, 12i; R(1) = ethyl, R2 = methyl, R(3) = CHO, R(4) = H), or hydroxymethyl (RTI-4587-055, 12g; R(1) = ethyl, R(2) = methyl, R(3) = CH2OH, R(4) = H) groups resulted in antispermatogenic compounds. Methyl ester 12b was an effective antifertility agent, without apparent effects on mating, when given orally to male mice at 7-15 mg/kg daily for 35 days. Further evaluation of these compounds as male contraceptive agents and probes for study of spermatogenesis appears warranted.

  DOI：

  10.1021/jm00005a003