(+/-)-Nordomesticine | 111467-61-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: (+/-)-Nordomesticine
• 英文别名: 2-methoxy-5,6,6a,7-tetrahydro-4H-benzo[de][1,3]dioxolo[4',5':4,5]benzo[1,2-g]quinolin-1-ol；18-Methoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaen-19-ol
• CAS: 111467-61-9
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: JWDBVEYVPQADLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (+/-)-N-trifluoroacetyldomesticine 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到(+/-)-Nordomesticine
  参考文献：
  名称：

  Hoshino, Osamu; Ogasawara, Hiromichi; Suzuki, Masaji, Heterocycles, 1987, vol. 25, p. 151 - 153

  摘要：

  DOI：

文献信息

• Structure–activity relationship studies with (±)-nantenine derivatives for α1-adrenoceptor antagonist activity
  作者：Bachtiar Indra、Kimihiro Matsunaga、Osamu Hoshino、Masaji Suzuki、Hiromichi Ogasawara、Yasushi Ohizumi

  DOI：10.1016/s0014-2999(02)01303-1

  日期：2002.2

  A series of (+/-)-nantenine derivatives of the natural aporphine alkaloids was synthesized and examined for a blocking action on a, adrenoceptors in rat aorta and A10-cells. The potency of these derivatives was compared with that of an aporphine-related compounds (+)boldine, an alpha(1)-adrenoceptor antagonist. Among nine (+/-)-nantenine derivatives having different substituents at N-6, C-1, or C-4 of the aporphine skeleton, (+/-)-domesticine had the most powerful ot alpha(1) -adrenoceptor-blocking action. The order of pA(2) values was (+/-)-domesticine (8.06 +/- 0.06)>(+/-)-nordomesticine (7.34 +/- 0.03)>(+/-)-nantenine(7.03 +/- 0.03)>(+)-boldine(6.91 +/- 0.02)> other derivatives. Study of the structure -activity relationships showed that the replacement of a methoxy moiety at C-1 position of (+/-)-nantenine with a hydroxyl group increased affinity for the receptor. In contrast, replacement of a methyl group with a hydrogen atom or an ethyl group at N-6 position in the (+/-)-nantenine structure decreased affinity for the receptor. These results suggest that a hydroxyl group at the C-1 position and a methyl group at the N-6 position in the (+/-)-nantenine structure are essential for the enhancement of affinity for the alpha(1)-adrenoceptor. (C) 2002 Elsevier Science B.V. All rights reserved.