1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol hydrochloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol hydrochloride
• 英文别名: 1-[(3,5-Diiodo-4-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-ium-6-ol;chloride
• 化学式: C₁₇H₁₇I₂NO₂*ClH
• 分子量: 557.597
• InChiKey: HIGTUHYRABQNCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  41.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol hydrochloride 在 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 三乙胺 、 calcium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-(3,5-diiodo-4-methoxybenzyl)-5,7-diiodo-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-6-ol
  参考文献：
  名称：

  Synthesis and Human β-Adrenoceptor Activity of 1-(3,5-Diiodo-4- methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol Derivatives in Vitro

  摘要：

  Trimetoquinol (I, TMQ) is a potent nonselective beta-adrenergic receptor (AR) agonist and a thromboxane A(2)/prostaglandin endoperoxide (TP) receptor antagonist, while 3',5'-diiodo-TMQ (2) exhibits beta(3)-AR selectivity. In search of selective beta(3)-AR agonists as potential drugs for the treatment of human obesity and type II diabetes mellitus, a series of 1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ols has been prepared and evaluated for their biological activities at human beta(1)-, beta(2)-, and beta(3)-ARs expressed in Chinese hamster ovary (CHO) cells. The compounds have been synthesized by the Bischler-Napieralski cyclization of corresponding amides followed by NaBH4 reduction, and the halogens in the aromatic ring A were introduced by direct halogenation of protected compound 11. Whereas halogen substitution in ring A reduced either potency or intrinsic activity on beta(3)-AR, the non-halogen-substituted compounds 8 and 10 were potent, selective, nearly full agonists for beta(3)-AR.

  DOI：

  10.1021/jm990463j