(2-amino-4-chloro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone | 701910-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-amino-4-chloro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone
• 英文别名: (2-Amino-4-chlorophenyl)-(3,4,5-trimethoxyphenyl)methanone
• CAS: 701910-48-7
• 化学式: C₁₆H₁₆ClNO₄
• 分子量: 321.76
• InChiKey: VDFJFCAVBXLKIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-羟基-2(5H)-呋喃酮 、 (2-amino-4-chloro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以91%的产率得到6-chloro-9-(3,4,5-trimethoxy-phenyl)-3H-furo[3,4-b]quinolin-1-one
  参考文献：
  名称：

  [DE] ANNELLIERTE CHINOLINDERIVATE ALS PESTIZIDE
  [EN] ANNELATED QUINOLINE DERIVATIVES AS PESTICIDE
  [FR] DERIVES DE QUINOLEINE ANNELES COMME PESTICIDES

  摘要：

  本发明申请涉及使用式（I）的喹啉衍生物，其中虚线结合代表单键或双键，并且取代基具有描述中所指定的含义，作为植物处理剂，特别用于对抗动物害虫；基于已知和新的螺环喹啉衍生物的植物处理剂和新的喹啉衍生物。

  公开号：

  WO2005097802A1
• 作为产物：
  描述：

  4-氯-2-硝基苯甲醛 在 盐酸 、 重铬酸吡啶 、 4 A molecular sieve 、 铁粉 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 (2-amino-4-chloro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 3-Aminobenzophenones as Antimitotic Agents

  摘要：

  A new series of 3-aminobenzophenone compounds as potent inhibitors of tubulin polymerization was discovered based on the mimic of the aminocombretastatin molecular skeleton. Lead compounds 5 and 11, with alkoxy groups at the C-4 position of B-ring, were potent cytotoxic agents and inhibitors of tubulin polymerization through the binding to the colchicine-binding site of tubulin. The corresponding antitubulin activities of 5 and 11 were similar to or greater than combretastatin A-4 and AVE-8063. Replacement of the methoxy group with a chloro group in the B ring of aminobenzopheneones (3, 8, and 9) caused drastic decrease in cytotoxic and antitubulin activity except in compounds 4 and 10, which could result from a unique alignment between chloro and amino groups located at the para position to each other. SAR information revealed that introduction of an amino group at the C-3 position in B ring of benzophenones, in addition to a methoxy group at the C-4 position, plays an important role for maximal cytotoxicity.

  DOI：

  10.1021/jm0305974

文献信息

• Annelated Quinoline Derivatives As Pesticide
  申请人：Velten Robert

  公开号：US20080113994A1

  公开（公告）日：2008-05-15

  The present filing of an invention relates to the use of quinoline derivatives of the formula in which the dashed bond is a single or double bond and the substituents have the definition given in the disclosure, as crop treatment compositions, particularly for controlling animal pests; to crop treatment compositions based on known and new annulated quinoline derivatives; and to new quinoline derivatives.

  本发明涉及使用式中虚线键为单键或双键，且取代基具有所述披露的定义的喹啉衍生物作为作物处理组合物，特别用于控制动物害虫；基于已知和新的环化喹啉衍生物的作物处理组合物；以及新的喹啉衍生物。
• Insecticidal heterolignans—Tubuline polymerization inhibitors with activity against chewing pests
  作者：Jens Frackenpohl、Isabelle Adelt、Horst Antonicek、Christian Arnold、Patricia Behrmann、Nicole Blaha、Jutta Böhmer、Oliver Gutbrod、Roman Hanke、Sabine Hohmann、Marc van Houtdreve、Peter Lösel、Olga Malsam、Martin Melchers、Valentina Neufert、Elisabeth Peschel、Udo Reckmann、Thomas Schenke、Hans-Peter Thiesen、Robert Velten、Kathrin Vogelsang、Hans-Christoph Weiss

  DOI：10.1016/j.bmc.2009.01.042

  日期：2009.6

  Starting from natural product podophyllotoxin 1 substituted heterolignans were identified with promising insecticidal in vivo activity. The impact of substitution in each segment of the core structure was investigated in a detailed SAR study, and variation of substituents in both aromatic moieties afforded derivatives 5 and 43 with broad insecticidal activity against lepidopteran and coleopteran species. In vitro measurements supported by modeling studies indicate that heterolignans 3-134 act as tubuline polymerization inhibitors interacting with the colchicine-binding site. Insect specific structure-activity effects were observed showing that the insecticidal SAR described herein differs from reported cytotoxicity studies. (C) 2009 Elsevier Ltd. All rights reserved.
• ANNELLIERTE CHINOLINDERIVATE ALS PESTIZIDE
  申请人：Bayer CropScience Aktiengesellschaft

  公开号：EP1735317A1

  公开（公告）日：2006-12-27