7,8-dihydro-3,6-didesoxymorphine | 69663-72-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 7,8-dihydro-3,6-didesoxymorphine
• 英文别名: 4,5α-epoxy-17-methyl-morphinane；(4R,4aR,7aS,12bS)-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline
• CAS: 69663-72-5
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: HWXKCCDLLDWFIH-UICACZKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-deoxy-7,8-dihydromorphine 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 78.0h， 生成 7,8-dihydro-3,6-didesoxymorphine
  参考文献：
  名称：

  Deoxymorphines: role of the phenolic hydroxyl in antinociception and opiate receptor interactions

  摘要：

  Several 3-deoxy opioids and 3,6-dideoxydihydromorphine was synthesized to ascertain the effect of the phenolic hydroxyl group on antinociceptive potency and receptor binding affinity. Catalytic reduction of the 3-tetrazolyl ether derivatives of dihydromorphine provided the entry into the 3-deoxydihydro series. The prototype, 3-deoxymorphine, was prepared by lithium aluminum hydride reduction of 3-deoxy-N-carbethoxymorphinone, obtained via its 7-(phenylseleno) derivative. 3-Deoxydihydromorphinone and 3,6-dideoxydihydromorphine were found to be about as potent as, or more potent than, morphine in standard antiociceptive assays. Each of them, however, was less potent than the comparable 3-hydroxy analogue, and their binding affinity to the opiate receptor was substantially decreased. The epoxy ring in 3.6-dideoxydihydromorphine was found to increase the antinociceptive potency of the compound.

  DOI：

  10.1021/jm00189a007

文献信息

• PROCESS FOR PREPARING MORPHINE COMPOUNDS
  申请人：Varghese Vimal

  公开号：US20150239860A1

  公开（公告）日：2015-08-27

  The present application relates to processes for the preparation of morphine compounds utilizing a novel intramolecular [4+2] cycloaddition reaction.

  本申请涉及利用一种新型分子内[4+2]环加成反应制备吗啡化合物的过程。
• PROCESS FOR THE PREPARATION OF MORPHINE ANALOGUES
  申请人：Patel Nileshkumar Sureshbhai

  公开号：US20110152527A1

  公开（公告）日：2011-06-23

  The present invention relates to an improved process for preparing morphinane analogues of formula (1) wherein the substituents R 1 , R 2 , R 2a , R 3 , R 4 , R 5 and Y have the meanings as defined in the specifications.

  本发明涉及一种改进的制备公式（1）中吗啡烷类似物的过程，其中取代基R1、R2、R2a、R3、R4、R5和Y的含义如规范中定义。
• PROCESS FOR THE PREPARATION OF MORPHINANE ANALOGUES
  申请人：Sun Pharmaceutical Industries Ltd.

  公开号：US20140031550A1

  公开（公告）日：2014-01-30

  The present invention relates to an improved process for preparing morphinane analogues of formula 1 wherein the substituents R 1 , R 2 , R 2a , R 3 , R 4 , R 5 and Y have the meanings as defined in the specifications.

  本发明涉及一种改进的制备公式1的吗啡烷类似物的过程，其中取代基R1、R2、R2a、R3、R4、R5和Y的含义如规范中所定义。
• Opioids and Efflux Transporters. Part 2: P-Glycoprotein Substrate Activity of 3- and 6-Substituted Morphine Analogs
  作者：Christopher W. Cunningham、Susan L. Mercer、Hazem E. Hassan、John R. Traynor、Natalie D. Eddington、Andrew Coop

  DOI：10.1021/jm701457j

  日期：2008.4.1

  Continuing our studies investigating opioids with reduced P-glycoprotein (P-gp) substrate activity, a series of known 3- and 6-hydroxy, -methoxy, and -desoxymorphine analogs was synthesized and analyzed for Pgp substrate activity and opioid binding affinity. 6-Desoxymorphine (7) showed high affinity for opioid receptors and did not induce P-gp-mediated ATP hydrolysis. Additionally, 7 demonstrated morphine-like antinociceptive potency in mice, indicating this compound as an ideal lead to further evaluate the role of P-gp in opioid analgesic tolerance development.
• US8546572B2
  申请人：——

  公开号：US8546572B2

  公开（公告）日：2013-10-01