2-nitro-3-trifluoromethylsulfonyloxy-N-cyclopropylmethylmorphinan | 1372134-47-8

• 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: 2-nitro-3-trifluoromethylsulfonyloxy-N-cyclopropylmethylmorphinan
• 英文别名: [(1R,9R,10R)-17-(cyclopropylmethyl)-5-nitro-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2,4,6-trien-4-yl] trifluoromethanesulfonate
• CAS: 1372134-47-8
• 化学式: C₂₁H₂₅F₃N₂O₅S
• 分子量: 474.501
• InChiKey: HASMCYRSXIFAJN-XAUMDUMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-nitro-3-trifluoromethylsulfonyloxy-N-cyclopropylmethylmorphinan 在 三乙基硅烷 、 1,3-双(二苯基膦)丙烷 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以53%的产率得到2-nitro-N-cyclopropylmethylmorphinan
  参考文献：
  名称：

  Synthesis, Binding Affinity, and Functional in Vitro Activity of 3-Benzylaminomorphinan and 3-Benzylaminomorphine Ligands at Opioid Receptors

  摘要：

  A series of 3-benzylamino-3-desoxymorphinan (I) and 3-benzylamino-3-desoxymorphine (II) derivatives were synthesized and evaluated for their binding affinities, and functional activity data are presented at MOR, KOR, and DOR Some of these ligands were found to have high binding affinity at MOR and KOR and displayed increased selectivity at MOR over KOR and DOR compared to butorphan or cyclorphan. The most selective compound, 3-(3'-hydroxybenzyl)amino-17-methylmorphinan (4g) (24-fold MOR to KOR and 1700-fold MOR to DOR) also showed high binding affinity (0.42 nM to MOR) and was a full agonist in the [S-35]GTP gamma S binding assay. 2-(3'-Hydroxybenzyl)amino-17-cyclopropylmethylmorphinan (17) was found to be a KOR-selective ligand (150-fold over MOR and > 10000-fold over the DORs). Most 3-benzylaminomorphinan derivatives were partial agonists at MOR and full agonists at KOR in the [S-35]GTP gamma S binding assay.

  DOI：

  10.1021/jm3001086
• 作为产物：
  描述：

  17-(环丙基甲基)吗喃-3-醇 在 甲酸 、 硝酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-nitro-3-trifluoromethylsulfonyloxy-N-cyclopropylmethylmorphinan
  参考文献：
  名称：

  Synthesis, Binding Affinity, and Functional in Vitro Activity of 3-Benzylaminomorphinan and 3-Benzylaminomorphine Ligands at Opioid Receptors

  摘要：

  A series of 3-benzylamino-3-desoxymorphinan (I) and 3-benzylamino-3-desoxymorphine (II) derivatives were synthesized and evaluated for their binding affinities, and functional activity data are presented at MOR, KOR, and DOR Some of these ligands were found to have high binding affinity at MOR and KOR and displayed increased selectivity at MOR over KOR and DOR compared to butorphan or cyclorphan. The most selective compound, 3-(3'-hydroxybenzyl)amino-17-methylmorphinan (4g) (24-fold MOR to KOR and 1700-fold MOR to DOR) also showed high binding affinity (0.42 nM to MOR) and was a full agonist in the [S-35]GTP gamma S binding assay. 2-(3'-Hydroxybenzyl)amino-17-cyclopropylmethylmorphinan (17) was found to be a KOR-selective ligand (150-fold over MOR and > 10000-fold over the DORs). Most 3-benzylaminomorphinan derivatives were partial agonists at MOR and full agonists at KOR in the [S-35]GTP gamma S binding assay.

  DOI：

  10.1021/jm3001086

文献信息

• Synthesis, Binding Affinity, and Functional in Vitro Activity of 3-Benzylaminomorphinan and 3-Benzylaminomorphine Ligands at Opioid Receptors
  作者：John L. Neumeyer、Bin Zhang、Tangzhi Zhang、Anna W. Sromek、Brian I. Knapp、Dana J. Cohen、Jean M. Bidlack

  DOI：10.1021/jm3001086

  日期：2012.4.26

  A series of 3-benzylamino-3-desoxymorphinan (I) and 3-benzylamino-3-desoxymorphine (II) derivatives were synthesized and evaluated for their binding affinities, and functional activity data are presented at MOR, KOR, and DOR Some of these ligands were found to have high binding affinity at MOR and KOR and displayed increased selectivity at MOR over KOR and DOR compared to butorphan or cyclorphan. The most selective compound, 3-(3'-hydroxybenzyl)amino-17-methylmorphinan (4g) (24-fold MOR to KOR and 1700-fold MOR to DOR) also showed high binding affinity (0.42 nM to MOR) and was a full agonist in the [S-35]GTP gamma S binding assay. 2-(3'-Hydroxybenzyl)amino-17-cyclopropylmethylmorphinan (17) was found to be a KOR-selective ligand (150-fold over MOR and > 10000-fold over the DORs). Most 3-benzylaminomorphinan derivatives were partial agonists at MOR and full agonists at KOR in the [S-35]GTP gamma S binding assay.