N-[(5R,6S)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl]-2-(3,4-dichlorophenyl)-N-methylacetamide hydrochloride | 152657-12-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-[(5R,6S)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl]-2-(3,4-dichlorophenyl)-N-methylacetamide hydrochloride
• 英文别名: N-[(4R,4aS,7S,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-2-(3,4-dichlorophenyl)-N-methylacetamide;hydrochloride
• CAS: 152657-12-0
• 化学式: C₂₉H₃₂Cl₂N₂O₄*ClH
• 分子量: 579.951
• InChiKey: ZSGROHPOPQXMDC-WVLARZQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  73.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二氯苯乙酸 、 6α-N-methylnaltrexamine 在 盐酸 作用下， 以58%的产率得到N-[(5R,6S)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl]-2-(3,4-dichlorophenyl)-N-methylacetamide hydrochloride
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationship of novel opioid κ-agonists

  摘要：

  By focusing on 4,5-epoxymorphinan, a traditional opioid skeleton but a new structure in the opioid kappa-agonist research field, and by rationally applying the 'message-address concept' and 'accessory site hypothesis,' we discovered a new chemical class opioid kappa- gonist, TRK-820 (1). Its development as an antipruritus is now in the final stage. Here, the full scope of its design, synthesis, and structure-activity relationship are described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.011

文献信息

• MORPHINAN DERIVATIVE AND MEDICINAL USE
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP0577847A1

  公开（公告）日：1994-01-12

  A morphinan derivative represented by general formula (1) or a pharmacologically acceptable acid addition salt thereof, an analgesic and diuretic containing the same as the active ingredient, and a process for producing the same The invention compound has potent analgesic and diuretic activities as a highly selective κ-opioid agonist, thus being useful as an analgesic and diuretic.

  一种由通式（1）代表的吗啡南衍生物或其药理上可接受的酸加成盐，一种含有吗啡南衍生物作为活性成分的镇痛剂和利尿剂，以及生产吗啡南衍生物的工艺。 本发明化合物作为一种高选择性κ-阿片激动剂，具有强效的镇痛和利尿活性，因此可用作镇痛剂和利尿剂。
• Morphinan derivative and its pharmaceutical applications
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP0846694A1

  公开（公告）日：1998-06-10

  A morphinan derivative represented by the general formula (I) or its pharmacologically acceptable acid addition salt:    wherein R5 is a specified cyclic ring, B is C1-14 alkylene and A is -XC(=Y)-, -XC(=y)z-, -X-, -XSO2- or -OC(OR4)(R4)- (where X is NCH3, NH, S or O, but is other than NCH3 when R6 and R7 together form -O-, each A, Y and Z, independently, is NR4, S or O and R4 is H, C1-5 alkyl or C6-12 aryl) have analgesic activity.

  由通式（I）或其药理学上可接受的酸加成盐代表的吗啡南衍生物： 其中 R5 为特定的环，B 为 C1-14 亚烷基，A 为 -XC(=Y)-、-XC(=y)z-、-X-、-XSO2- 或 -OC(OR4)(R4)-（其中 X 为 NCH3、NH、S 或 O，但当 R6 和 R7 共同形成 -O- 时为 NCH3 以外，每个 A、Y 和 Z 独立地为 NR4、S 或 O，R4 为 H、C1-5 烷基或 C6-12 芳基）具有镇痛活性。
• US6177438B1
  申请人：——

  公开号：US6177438B1

  公开（公告）日：2001-01-23
• US6277859B1
  申请人：——

  公开号：US6277859B1

  公开（公告）日：2001-08-21
• US6323212B1
  申请人：——

  公开号：US6323212B1

  公开（公告）日：2001-11-27