desoxydihydrothebainone ethylene glycol ketal | 100837-77-2

• 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: desoxydihydrothebainone ethylene glycol ketal
• 英文别名: 3-methoxy-17-methylmorphinan-6-spiro-2'-(1',3'-dioxolane)；(1'S,9'R,10'R)-4'-methoxy-17'-methylspiro[1,3-dioxolane-2,13'-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene]
• CAS: 100837-77-2
• 化学式: C₂₀H₂₇NO₃
• 分子量: 329.439
• InChiKey: YBAAMDKMCNQZGQ-UHOSZYNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  desoxydihydrothebainone ethylene glycol ketal 在 盐酸 、 氢溴酸 、 溴 、 氯甲酸乙酯 、 碳酸氢钠 、 potassium carbonate 、 溶剂黄146 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 101.0h， 生成 (1S,9R,10R)-20-(cyclobutylmethyl)-15-methoxy-6-thia-4,20-diazapentacyclo[8.7.3.01,9.03,7.012,17]icosa-3(7),4,12(17),13,15-pentaen-5-amine
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of 6,7-Indolo/Thiazolo-MorphinansFurther SAR of Levorphanol

  摘要：

  To further extend the structure-activity relationships of levorphanol, two series of novel morphinans were prepared by incorporation of an indole or aminothiazole fragment to the hexyl ring (ring C) in levorphanol. Such morphinans differed from previously reported ligands in that such indole- or aminothiazole-containing morphinans displayed enhanced binding affinity to the delta opioid receptor, while the affinity to kappa and mu receptors was slightly reduced.

  DOI：

  10.1021/jm0701674
• 作为产物：
  描述：

  二氢可待因酮 在 吡啶 、 盐酸 、 氨 、 sodium 、 铜 、 caesium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 锌 作用下， 以 甲苯 、 苯 为溶剂， 反应 11.0h， 生成 desoxydihydrothebainone ethylene glycol ketal
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of 6,7-Indolo/Thiazolo-MorphinansFurther SAR of Levorphanol

  摘要：

  To further extend the structure-activity relationships of levorphanol, two series of novel morphinans were prepared by incorporation of an indole or aminothiazole fragment to the hexyl ring (ring C) in levorphanol. Such morphinans differed from previously reported ligands in that such indole- or aminothiazole-containing morphinans displayed enhanced binding affinity to the delta opioid receptor, while the affinity to kappa and mu receptors was slightly reduced.

  DOI：

  10.1021/jm0701674

文献信息

• Synthesis of quinolinomorphinan-4-ol derivatives as δ opioid receptor agonists
  作者：Yoshihiro Ida、Toru Nemoto、Shigeto Hirayama、Hideaki Fujii、Yumiko Osa、Masayuki Imai、Takashi Nakamura、Toshiyuki Kanemasa、Akira Kato、Hiroshi Nagase

  DOI：10.1016/j.bmc.2011.11.047

  日期：2012.1

  The previously reported morphinan derivative SN-28 showed high selectivity and agonist activity for the delta opioid receptor. In the course of examining the structure-activity relationship of SN-28 derivatives, the derivatives with the 4-hydroxy group (SN-24, 26, 27) showed higher selectivities for the 8 receptor over the mu receptor than the corresponding SN-28 derivatives with the 3-hydroxy group (SN-11, 23, 28). Derivatives with the 4-hydroxy group showed potent agonist activities for the 5 receptor in the [S-35]GTPyS binding assay. Although the 17-cyclopropylmethyl derivative (SN-11) with a 3-hydroxy group showed the lowest selectivity for the delta receptor among the morphinan derivatives, the agonist activity toward the delta receptor was the most potent for candidates with the 3-hydroxy group. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and Pharmacological Evaluation of 6,7-Indolo/Thiazolo-MorphinansFurther SAR of Levorphanol
  作者：Ao Zhang、Fuying Li、Chunyong Ding、Qizhen Yao、Brian I. Knapp、Jean M. Bidlack、John L. Neumeyer

  DOI：10.1021/jm0701674

  日期：2007.5.1

  To further extend the structure-activity relationships of levorphanol, two series of novel morphinans were prepared by incorporation of an indole or aminothiazole fragment to the hexyl ring (ring C) in levorphanol. Such morphinans differed from previously reported ligands in that such indole- or aminothiazole-containing morphinans displayed enhanced binding affinity to the delta opioid receptor, while the affinity to kappa and mu receptors was slightly reduced.