N-(2-(1H-pyrazol-1-yl)phenyl)-2,3-dihydrobenzofuran-7-carboxamide | 883120-58-9

• 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: N-(2-(1H-pyrazol-1-yl)phenyl)-2,3-dihydrobenzofuran-7-carboxamide
• 英文别名: N-(2-pyrazol-1-ylphenyl)-2,3-dihydro-1-benzofuran-7-carboxamide
• CAS: 883120-58-9
• 化学式: C₁₈H₁₅N₃O₂
• 分子量: 305.336
• InChiKey: AJGWNZASJZYKCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二氢-1-苯并呋喃-7-碳酰氯 、 2-1H-吡唑苯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(2-(1H-pyrazol-1-yl)phenyl)-2,3-dihydrobenzofuran-7-carboxamide
  参考文献：
  名称：

  Discovery of N-aryl-9-oxo-9H-fluorene-1-carboxamides as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 2. Structure–activity relationships of the 9-oxo-9H-fluorene ring

  摘要：

  As a continuation of our studies of apoptosis inducing 9-oxo-9H-fluorene-1-carboxamides as potential anticancer agents, we explored modi. cation of the 9-oxo-9H-fluorene ring. SAR studies showed that most changes to the 9-oxo-9H-fluorene ring were not well tolerated, except the 9H-fluorene (2b) and dibenzothiophene (2d) analogs, which were about twofold less active than the 9-oxo-9H-fluorene analog 2a. Significantly, introduction of substitutions at the 7-position of the 9-oxo-9H-fluorene ring led to compounds 5a-5c with improved activity. Compound 5a was found to have EC50 values of 0.15-0.29 mu M against T47D, HCT116, and SNU398 cells, about fivefold more potent than the original lead 2a. As opposed to the original lead compound 2a, compounds 5a-5b were active in a tubulin inhibition assay, indicating a change of mechanism of action. The potent azido analog 5c could be utilized for target identification. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.11.025

文献信息

• Substituted N-Aryl-9-Oxo-9H-Fluorene-1-Carboxamides and Analogs as Activators of Caspases and Inducers of Apoptosis
  申请人：Kemnitzer E. William

  公开号：US20080096848A1

  公开（公告）日：2008-04-24

  The present invention is directed to substituted N-aryl-9-oxo-9H-fluorene-1-carboxamides and analogs thereof, represented by the general Formula I: (I) wherein R 1 -R 8 , X and Ar are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及取代的N-芳基-9-氧代-9H-芴-1-羧酰胺及其类似物，由通式I表示：（I）其中R1-R8、X和Ar的定义如本文所述。本发明还涉及发现具有I式化合物的化合物是caspase的活化剂和凋亡诱导剂。因此，本发明的caspase活化剂和凋亡诱导剂可用于在发生异常细胞的无控制生长和扩散的各种临床情况下诱导细胞死亡。
• SUBSTITUTED N-ARYL-9-OXO-9H-FLUORENE-1-CARBOXAMIDES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS
  申请人：Cytovia, Inc.

  公开号：EP1804786A2

  公开（公告）日：2007-07-11
• EP1804786A4
  申请人：——

  公开号：EP1804786A4

  公开（公告）日：2008-01-02
• [EN] SUBSTITUTED N-ARYL-9-OXO-9H-FLUORENE-1-CARBOXAMIDES AND ANALOGS AS ACTIVATOR OF CASPASES AND INDUCERS OF APOPTOSIS<br/>[FR] N-ARYL-9-OXO-9H-FLUORENE-1-CARBOXAMIDES SUBSTITUES ET ANALOGUES UTILISES COMME ACTIVATEURS DES CASPASES ET INDUCTEURS DE L'APOPTOSE
  申请人：CYTOVIA INC

  公开号：WO2006039356A2

  公开（公告）日：2006-04-13

  The present invention is directed to substituted N-aryl-9-oxo-9H-fluorene-1-carboxamides and analogs thereof, represented by the general Formula I: (I) wherein R1-R8, X and Ar are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.