6-Acetylamino-1-benzo[1,3]dioxol-5-ylmethyl-7-methoxy-3,4-dihydro-isoquinoline-3-carboxylic acid ethyl ester | 597544-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 6-Acetylamino-1-benzo[1,3]dioxol-5-ylmethyl-7-methoxy-3,4-dihydro-isoquinoline-3-carboxylic acid ethyl ester
• CAS: 597544-06-4
• 化学式: C₂₃H₂₄N₂O₆
• 分子量: 424.453
• InChiKey: OEERLYHTJPDXTH-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  6-Acetylamino-1-benzo[1,3]dioxol-5-ylmethyl-7-methoxy-3,4-dihydro-isoquinoline-3-carboxylic acid ethyl ester 在 selenium(IV) oxide 、 氢溴酸 、 sulfur 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-(Benzo[1,3]dioxole-5-carbonyl)-7-hydroxy-6-methanesulfonylamino-isoquinoline-3-carboxylic acid
  参考文献：
  名称：

  6,7-Dihydroxyisoquinoline-3-carboxylic acids are potent inhibitors on the binding of insulin-Like growth factor (IGF) to IGF-binding proteins: optimization of the 1-position benzoyl side chain

  摘要：

  A series of 1-benzoyl isoquinolines, based on compound 1, was synthesized and evaluated for their ability to displace IGF-I from its complex with IGF-binding protein-3. Successful modifications of I included the replacement of the 3,4-dihydroxy-benzoyl group with a substituted benzyl group. These alternations culminated in the discovery of compounds such as 7o which had excellent in vitro potency (K-i = 9.4 nM) but with one less of the labile catechol functionality of 1. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00321-4
• 作为产物：
  描述：

  2-(2-Benzo[1,3]dioxol-5-yl-acetylamino)-3-(4-methoxy-3-nitro-phenyl)-propionic acid ethyl ester 在 palladium on activated charcoal 氢气 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 生成 6-Acetylamino-1-benzo[1,3]dioxol-5-ylmethyl-7-methoxy-3,4-dihydro-isoquinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  6,7-Dihydroxyisoquinoline-3-carboxylic acids are potent inhibitors on the binding of insulin-Like growth factor (IGF) to IGF-binding proteins: optimization of the 1-position benzoyl side chain

  摘要：

  A series of 1-benzoyl isoquinolines, based on compound 1, was synthesized and evaluated for their ability to displace IGF-I from its complex with IGF-binding protein-3. Successful modifications of I included the replacement of the 3,4-dihydroxy-benzoyl group with a substituted benzyl group. These alternations culminated in the discovery of compounds such as 7o which had excellent in vitro potency (K-i = 9.4 nM) but with one less of the labile catechol functionality of 1. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00321-4