(2R)-N-(4-phenoxybenzyl)-3-cyclohexylmethylthio-2-((4R)-thiazolidin-4-ylcarbonylamino)propanamide | 219626-50-3

• 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: (2R)-N-(4-phenoxybenzyl)-3-cyclohexylmethylthio-2-((4R)-thiazolidin-4-ylcarbonylamino)propanamide
• 英文别名: (R)-Thiazolidine-4-carboxylic acid [(R)-2-cyclohexylmethylsulfanyl-1-(4-phenoxy-benzylcarbamoyl)-ethyl]-amide；(4R)-N-[(2R)-3-(cyclohexylmethylsulfanyl)-1-oxo-1-[(4-phenoxyphenyl)methylamino]propan-2-yl]-1,3-thiazolidine-4-carboxamide
• CAS: 219626-50-3
• 化学式: C₂₇H₃₅N₃O₃S₂
• 分子量: 513.725
• InChiKey: XDJJQUQBFLGQCK-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲氧基乙酰氯 、 (2R)-N-(4-phenoxybenzyl)-3-cyclohexylmethylthio-2-((4R)-thiazolidin-4-ylcarbonylamino)propanamide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2R)-N-(4-phenoxybenzyl)-3-cyclohexylmethylthio-2-((4R)-3-methoxymethyl carbonylthiazolidin-4-ylcarbonylamino) propanamide
  参考文献：
  名称：

  EP1097929

  摘要：

  公开号：
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-S-cyclohexylmethyl-L-cysteine 在 盐酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 (2R)-N-(4-phenoxybenzyl)-3-cyclohexylmethylthio-2-((4R)-thiazolidin-4-ylcarbonylamino)propanamide
  参考文献：
  名称：

  Structure–Activity Study of l -Cysteine-Based N-Type Calcium Channel Blockers: Optimization of N- and C-Terminal Substituents

  摘要：

  Synthesis and structure-activity relationship (SAR) studies of L-cysteine-based N-type calcium channel blockers are described. In the course of exploring SAR of the N- and C-terminal substituents, the L-cysteine derivative 4b was found to be a potent N-type calcium channel blocker with an IC50 value of 0.14 muM on IMR-32 assay. Compound 4b showed 12-fold selectivity for N-type over L-type calcium channels on AtT-20 assay. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00032-x

文献信息

• Amino acid derivatives
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：US20030013725A1

  公开（公告）日：2003-01-16

  A compound of the formula (1): 1 [wherein R 1 is (substituted) alkyl, alkoxy, phenyl, hetero ring etc.; A is bond, CO, SO 2 ; R 2 is H, (substituted) alkyl etc.; D is alkylene etc.; E is COO, OCO, O, S, SO, SO 2 etc.; R 3 is (substituted) alkyl, carbocyclic ring, hetero ring; J is O, NR 16 (R 16 is H, substituted alkyl); R 4 is (substituted) alkyl, carbocyclic ring, hetero ring.] or non-toxic salt thereof, and an N-type calcium channel blocker comprising it as an active ingredient. The compounds of the formula (I) possess an inhibitory action on N-type calcium channel, so they are useful as agent for the prevention and/or treatment of cerebral infarct, transient ischemic attack, encephalomyelopathy after cardiac operation, spinal angiopathy, hypertension with stress, neurosis or epilepsy etc. or agent for the treatment of pain.

  化合物的式子（1）：1[其中R1是（取代）烷基，烷氧基，苯基，杂环等；A是键，CO，SO2；R2是H，（取代）烷基等；D是烷基等；E是COO，OCO，O，S，SO，SO2等；R3是（取代）烷基，环烷基，杂环；J是O，NR16（R16是H，取代烷基）；R4是（取代）烷基，环烷基，杂环。或其非毒性盐，以及作为活性成分的N型钙通道阻滞剂。式（I）的化合物具有对N型钙通道的抑制作用，因此它们可用作预防和/或治疗脑梗死、短暂性脑缺血发作、心脏手术后脑脊髓病、脊髓血管病、应激性高血压、神经症或癫痫等的药物或治疗疼痛的药物。
• AMINO ACID DERIVATIVES
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：EP0997147A1

  公开（公告）日：2000-05-03

  A compound of the formula (I): [wherein R1 is (substituted) alkyl, alkoxy, phenyl, hetero ring etc.; A is bond, CO, SO2; R2 is H, (substituted) alkyl etc.; D is alkylene etc.; E is COO, OCO, O, S, SO, SO2 etc.; R3 is (substituted) alkyl, carbocyclic ring, hetero ring; J is O, NR16 (R16 is H, substituted alkyl); R4 is (substituted) alkyl, carbocyclic ring, hetero ring.] or non-toxic salt thereof, and an N-type calcium channel blocker comprising it as an active ingredient. The compounds of the formula (I) possess an inhibitory action on N-type calcium channel, so they are useful as agent for the prevention and/or treatment of cerebral infarct, transient ischemic attack, encephalomyelopathy after cardiac operation, spinal angiopathy, hypertension with stress, neurosis or epilepsy etc. or agent for the treatment of pain.

  式 (I) 的化合物： [其中 R1 是（取代）烷基、烷氧基、苯基、杂环等；A 是键、CO、SO2；R2 是 H、（取代）烷基等；D 是亚烷基等；E 是 COO、OCO、O、S、SO、SO2 等。R3是（取代的）烷基、碳环、杂环；J是O、NR16（R16是H、取代的烷基）；R4是（取代的）烷基、碳环、杂环]或其无毒盐，以及包含其作为活性成分的N型钙通道阻滞剂。 式（I）化合物对 N 型钙通道具有抑制作用，因此可作为预防和/或治疗脑梗塞、短暂性脑缺血发作、心脏手术后脑脊髓病变、脊髓血管病变、应激性高血压、神经官能症或癫痫等疾病的药物或治疗疼痛的药物。
• AMINO ACID DERIVATIVES AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1097929A1

  公开（公告）日：2001-05-09

  The present invention relates to the compounds of the formula (I) and salts thereof (all the symbols are the same meanings as described in the specification). The compounds of the formula (I) possess inhibitory activity of N-type calcium channel, so they are useful as drug for prevention and/or treatment of cerebral infarct, transient ischemic attack, encephalomyelopathy after cardiac operation, spinal angiopathy, hypertension with stress, neurosis, epilepsy, asthma and pollakiuria etc. or agent for the treatment of pain.

  本发明涉及式（I）化合物及其盐类（所有符号的含义与说明书中所述相同）。 式（I）化合物具有抑制 N 型钙通道的活性，因此可作为预防和/或治疗脑梗塞、短暂性脑缺血发作、心脏手术后脑脊髓病变、脊髓血管病变、应激性高血压、神经官能症、癫痫、哮喘和花粉尿症等疾病的药物或治疗疼痛的制剂。
• Amino acid derivatives and pharmaceutical composition comprising, as active ingredients, them
  申请人：Seko Takuya

  公开号：US20050009890A1

  公开（公告）日：2005-01-13

  The present invention relates to the compounds of the formula (I) and salts thereof (all the symbols are the same meanings as described in the specification). The compounds of the formula (I) possess inhibitory activity of N-type calcium channel, so they are useful as drug for prevention and/or treatment of cerebral infarct, transient ischemic attack, encephalomyelopathy after cardiac operation, spinal angiopathy, hypertension with stress, neurosis, epilepsy, asthma and pollakiuria etc. or agent for the treatment of pain.
• US6903119B1
  申请人：——

  公开号：US6903119B1

  公开（公告）日：2005-06-07