7-甲氧基-5-硝基-1-苯并呋喃-2-羧酸 | 25672-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 7-甲氧基-5-硝基-1-苯并呋喃-2-羧酸
• 英文名称: 7-methoxy-5-nitro-benzofuran-2-carboxylic acid
• 英文别名: 7-Methoxy-5-nitro-1-benzofuran-2-carboxylic acid
• CAS: 25672-29-1
• 化学式: C₁₀H₇NO₆
• 分子量: 237.169
• InChiKey: IOZHCNSHXMWQNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-甲氧基-5-硝基-1-苯并呋喃-2-羧酸 在 palladium/alumina 氢气 、 乙酰氯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 64.0h， 生成 Methyl 5-[(2-methylpropan-2-yl)oxycarbonylamino]-7-phenylmethoxy-1-benzofuran-2-carboxylate
  参考文献：
  名称：

  Total Synthesis of Seco (+)- and ent-(−)-Oxaduocarmycin SA:  Construction of the (Chloromethyl)indoline Alkylating Subunit by a Novel Intramolecular Aryl Radical Cyclization onto a Vinyl Chloride

  摘要：

  A practical, total synthesis of seco-(+)-oxaduocarmycin 3a, an analogue of the highly cytotoxic natural product, duocarmycin SA (1), is described. The 13-step synthesis features a novel and efficient intramolecular aryl radical cyclization onto a vinyl chloride as a direct entry to the (chloromethyl)indoline alkylating subunit 14. Subsequent resolution, utilizing a preparative Chiralpak AD column, provided enantiomerically pure alkylating subunits 14a and 14b which were elaborated to seco-(+) and ent-(-)-oxaduocarmycins, 3a and 3b, respectively. The natural enantiomer 3a was active at pM concentrations and exhibited 7-50-fold higher potentcy than its enantiomer 3b in in vitro cytotoxicity assays.

  DOI：

  10.1021/jo971880b
• 作为产物：
  描述：

  2-(2-甲酰基-6-甲氧基-4-硝基苯氧基)乙酸乙酯 在 吡啶盐酸盐 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 7-甲氧基-5-硝基-1-苯并呋喃-2-羧酸
  参考文献：
  名称：

  Total Synthesis of Seco (+)- and ent-(−)-Oxaduocarmycin SA:  Construction of the (Chloromethyl)indoline Alkylating Subunit by a Novel Intramolecular Aryl Radical Cyclization onto a Vinyl Chloride

  摘要：

  A practical, total synthesis of seco-(+)-oxaduocarmycin 3a, an analogue of the highly cytotoxic natural product, duocarmycin SA (1), is described. The 13-step synthesis features a novel and efficient intramolecular aryl radical cyclization onto a vinyl chloride as a direct entry to the (chloromethyl)indoline alkylating subunit 14. Subsequent resolution, utilizing a preparative Chiralpak AD column, provided enantiomerically pure alkylating subunits 14a and 14b which were elaborated to seco-(+) and ent-(-)-oxaduocarmycins, 3a and 3b, respectively. The natural enantiomer 3a was active at pM concentrations and exhibited 7-50-fold higher potentcy than its enantiomer 3b in in vitro cytotoxicity assays.

  DOI：

  10.1021/jo971880b

文献信息

• 2-Heteroarylcarboxylic acid amides
  申请人：Hendrix Martin

  公开号：US20050119325A1

  公开（公告）日：2005-06-02

  The invention relates to novel 2-heteroarylcarboxamides, processes for their preparation, and their use for producing medicaments for the treatment and/or prophylaxis of diseases and for improving perception, concentration, learning and/or memory.

  本发明涉及新型2-杂环芳基甲酰胺、其制备方法以及用于制备治疗和/或预防疾病以及改善感知、注意力、学习和/或记忆的药物的用途。
• 2-HETEROARYLCARBOXYLIC ACID AMIDES
  申请人：Hendrix Martin

  公开号：US20100222378A1

  公开（公告）日：2010-09-02

  The invention relates to novel 2-heteroarylcarboxamides, processes for their preparation, and their use for producing medicaments for the treatment and/or prophylaxis of diseases and for improving perception, concentration, learning and/or memory.

  该发明涉及新型2-杂环芳基甲酰胺、其制备方法及其用于制备治疗和/或预防疾病以及改善感知、注意力、学习和/或记忆的药物。
• 2-HETEROARYLCARBONSÄUREAMIDE
  申请人：Bayer HealthCare AG

  公开号：EP1461335B1

  公开（公告）日：2007-02-28
• US7732477B2
  申请人：——

  公开号：US7732477B2

  公开（公告）日：2010-06-08
• US8076355B2
  申请人：——

  公开号：US8076355B2

  公开（公告）日：2011-12-13