1-[(3,5-Diiodo-4-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-6-ol

• 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-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-6-ol
• 化学式: C₁₇H₁₇I₂NO₂
• 分子量: 521.136
• InChiKey: BAENDFBYSDBIFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 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：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-苯氧基苯乙胺 在 盐酸 、 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 10.5h， 生成 1-[(3,5-Diiodo-4-methoxyphenyl)methyl]-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

文献信息

• Use of a beta-3 agonist for the treatment of disorders of the prostate and of the lower urogenital tract
  申请人：Michel Christian Martin

  公开号：US20060084700A1

  公开（公告）日：2006-04-20

  This invention describes the use of beta-3-adrenoceptor agonists for the treatment of disorders associated with the prostate. These include disorders like those occurring in a prostatitis, where attributable to inflammatory processes or chronic irritation, or disorders like those associated with benign changes of the prostate. The invention is particularly suitable for the treatment of benign prostatic hyperplasia (BPH).

  本发明描述了使用β-3肾上腺素受体激动剂治疗与前列腺有关的疾病。这些疾病包括由炎症过程或慢性刺激引起的前列腺炎等疾病，或与前列腺良性病变有关的疾病。本发明尤其适用于治疗良性前列腺增生症（BPH）。
• Synthesis and Human β-Adrenoceptor Activity of 1-(3,5-Diiodo-4- methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol Derivatives in Vitro
  作者：Yali He、Victor I. Nikulin、Sandeep S. Vansal、Dennis R. Feller、Duane D. Miller

  DOI：10.1021/jm990463j

  日期：2000.2.1

  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.