2-acetamido-4-(3',5'-diiodo-4'-methoxyphenylmethyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine | 221658-96-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-acetamido-4-(3',5'-diiodo-4'-methoxyphenylmethyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine
• 英文别名: N-[4-[(3,5-diiodo-4-methoxyphenyl)methyl]-4,5,6,7-tetrahydro-[1,3]thiazolo[5,4-c]pyridin-2-yl]acetamide
• CAS: 221658-96-4
• 化学式: C₁₆H₁₇I₂N₃O₂S
• 分子量: 569.205
• InChiKey: RAENECWVHIAJHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  顺丁烯二酸 、 2-acetamido-4-(3',5'-diiodo-4'-methoxyphenylmethyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine 以 乙腈 为溶剂， 生成 2-acetamido4-(3',5'-diiodo-4'-methoxyphenylmethyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine maleate
  参考文献：
  名称：

  Beta3-Adrenoreceptor agonists, agonist compositions and methods of using

  摘要：

  该发明提供了β3-肾上腺素受体激动剂，包括β3-肾上腺素受体激动剂化合物的药物组合物，以及使用这些化合物来刺激、调节或调节动物脂肪组织中脂肪代谢的方法。

  公开号：

  US20040019079A1
• 作为产物：
  描述：

  2-[2-(2-amino-1,3-thiazol-4-yl)ethyl]-1H-isoindole-1,3(2H)-dione hydrobromide 在 sodium hydroxide 、 sodium tetrahydroborate 、 氢溴酸 、 三氯氧磷 作用下， 以 甲醇 、 氯仿 、 乙腈 、 苯 为溶剂， 反应 9.0h， 生成 2-acetamido-4-(3',5'-diiodo-4'-methoxyphenylmethyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine
  参考文献：
  名称：

  2-Amino-4-benzyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridines:  Novel Selective β₃-Adrenoceptor Agonists

  摘要：

  Trimetoquinol (TMQ, 7) is a potent nonselective beta-adrenoceptor (AR) agonist. Replacement of the catechol moiety of TMQ with a 2-aminothiazole group resulted in novel thiazolopyridine derivatives 9-11 which have been synthesized and evaluated for biological activity on human beta(1)-, beta(2)-, and beta(3)-AR. The Bisckler-Napieralski reaction has been employed as a novel approach to construct the 2-amino-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine ring system. Although in radioligand binding studies analogues 9 and 10 did not show selectivity toward beta(3)-AR, they exhibited a high degree of selective beta(3)-AR agonist activity in functional assays. Moreover, the beta(3)-AR agonist activity of the 2-aminothiazole derivatives is abolished by N-acetylation (analogue 11) or ring opening (analogue 25). This illustrates the importance of the intact 2-amino-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine ring for beta(3)-AR activity.

  DOI：

  10.1021/jm990012z

文献信息

• Beta3-Adrenoreceptor agonists, agonist compositions and methods of using
  申请人：——

  公开号：US20040019079A1

  公开（公告）日：2004-01-29

  The invention provides &bgr; 3 -adrenoreceptor agonists, pharmaceutical compositions comprising &bgr; 3 -adrenoreceptor agonist compounds, and methods of using such compounds for stimulating, regulating or modulating metabolism of fats in adipose tissue in animals.

  该发明提供了β3-肾上腺素受体激动剂，包括β3-肾上腺素受体激动剂化合物的药物组合物，以及使用这些化合物来刺激、调节或调节动物脂肪组织中脂肪代谢的方法。
• 2-Amino-4-benzyl-4,5,6,7-tetrahydrothiazolo[5,4-<i>c</i>]pyridines:  Novel Selective β₃-Adrenoceptor Agonists
  作者：Weiping Zheng、Victor I. Nikulin、Anish A. Konkar、Sandeep S. Vansal、Gamal Shams、Dennis R. Feller、Duane D. Miller

  DOI：10.1021/jm990012z

  日期：1999.6.1

  Trimetoquinol (TMQ, 7) is a potent nonselective beta-adrenoceptor (AR) agonist. Replacement of the catechol moiety of TMQ with a 2-aminothiazole group resulted in novel thiazolopyridine derivatives 9-11 which have been synthesized and evaluated for biological activity on human beta(1)-, beta(2)-, and beta(3)-AR. The Bisckler-Napieralski reaction has been employed as a novel approach to construct the 2-amino-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine ring system. Although in radioligand binding studies analogues 9 and 10 did not show selectivity toward beta(3)-AR, they exhibited a high degree of selective beta(3)-AR agonist activity in functional assays. Moreover, the beta(3)-AR agonist activity of the 2-aminothiazole derivatives is abolished by N-acetylation (analogue 11) or ring opening (analogue 25). This illustrates the importance of the intact 2-amino-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine ring for beta(3)-AR activity.