4-(环己基氨基)-2H-1-苯并吡喃-2-酮 | 127202-76-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 4-(环己基氨基)-2H-1-苯并吡喃-2-酮
• 英文名称: 4-cyclohexylaminocoumarin
• 英文别名: 4-(Cyclohexylamino)chromen-2-one
• CAS: 127202-76-0
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: RLIXVONFOXAXLN-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C
• 沸点：
  424.2±34.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(环己基氨基)-2H-1-苯并吡喃-2-酮 、 2-甲基苄溴 反应 8.0h， 以51%的产率得到4-cyclohexylamino-3-(2-methyl-benzyl)-chromen-2-one
  参考文献：
  名称：

  Synthesis, structure, and estrogenic activity of 4-amino-3-(2-methylbenzyl)coumarins on human breast carcinoma cells

  摘要：

  A number of coumarins exhibit interesting pharmacological activities and are therefore of therapeutic use. We report here the synthesis and the structural analysis of new N-substituted 4-amino-3-(2-methylbenzyl)coumarins (compounds 8a-8e) that present structural analogies with estrothiazine and 11- or 7-substituted 17 beta-estradiol. These derivatives were tested with respect to estrogenic activity on the estrogen receptor positive (ER+) human MCF-7 breast cancer cell line. Two of the reported compounds (8a and 8b) stimulated specifically the proliferation of MCF-7 cells, but not that of estrogen receptor negative (ER-) human MDA-MB-231 breast cancer cells, suggesting that their mitogenic activity is mediated by ER. Accordingly, the stimulating effect of 8a and 8b was suppressed by the pure antiestrogen fulvestrant. Besides, 8a and 8b induced ER down-regulation similar to that produced by classical ER agonists or pure antagonists. The effects of the compounds under study on ER-mediated transcription were assessed on (ER+) MVLN cells, that is, MCF-7 cells stably transfected with a pVit-tk-Luc reporter plasmid. Derivatives 8a and 8b, and surprisingly compound 8c, enhanced ER-mediated gene transactivation in that model. Finally, no coumarin was able to compete with tritiated 17 beta-estradiol ([H-3]E-2) for ER binding, suggesting unconventional interactions with the receptor, such as interactions with the second binding pocket or with the coactivator-binding region. To conclude, observations performed in this study on compound 8c reveal that estrogenic activity can be dissociated from enhancement of cell proliferation. Furthermore, ERE-driven transactivation of transcription seems to be a condition necessary, but not sufficient, for estrogen-induced stimulation of cell growth. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.025
• 作为产物：
  描述：

  4-羟基香豆素 、 环己胺 反应 0.01h， 以92%的产率得到4-(环己基氨基)-2H-1-苯并吡喃-2-酮
  参考文献：
  名称：

  Chavan, Abhijit P., Journal of Chemical Research, 2006, # 3, p. 179 - 181

  摘要：

  DOI：

文献信息

• Facile and eco-friendly synthesis of chromeno[4,3-b]pyrrol-4(1H)-one derivatives applying magnetically recoverable nano crystalline CuFe₂O₄ involving a domino three-component reaction in aqueous media
  作者：Moumita Saha、Koyel Pradhan、Asish R. Das

  DOI：10.1039/c6ra06979g

  日期：——

  Nanocrystalline CuFe2O4 catalyzed one pot three component synthesis of chromeno[4,3-b]pyrrol-4(1H)-one derivatives has been achieved in aqueous media. The reaction between the essential building blocks (amine, glyoxal monohydrate and 4-aminocoumarin) has been performed at low catalyst loading, leading to a high yield of the desired heterocyclic scaffold. CuFe2O4 magnetic nanoparticles were prepared

  纳米晶CuFe 2 O 4在水性介质中催化一锅三组分合成铬诺[4,3 - b ]吡咯-4（1 H）-一衍生物。基本组成部分（胺，乙二醛一水合物和4-氨基香豆素）之间的反应已在低催化剂负载量下进行，从而导致所需杂环骨架的高收率。采用简单有效的柠檬酸络合物法制备了CuFe 2 O 4磁性纳米粒子，并利用XRD，FT-IR，EDX，TEM和HRTEM进行了表征。催化剂的易于回收和再利用以及该方法的操作简单性使该方案具有吸引力，可持续性和经济性。
• Synthesis of 4-(Monoalkylamino)-coumarins
  作者：Ivo C. Ivanov、Stoyan K. Karagiosov、Ilia Manolov

  DOI：10.1002/ardp.19913240118

  日期：——
• BADRAN, M. M.;EL-ANSARI, A. K.;EL-MELIGIE, S., EGYPT. J. PHARM. SCI., 30,(1989) N-4, C. 379-387
  作者：BADRAN, M. M.、EL-ANSARI, A. K.、EL-MELIGIE, S.

  DOI：——

  日期：——
• IVANOV, IVO C.;KARAGIOSOV, STOYAN K.;MANOLOV, ILIA, ARCH. PHARM., 324,(1991) N, C. 61-62
  作者：IVANOV, IVO C.、KARAGIOSOV, STOYAN K.、MANOLOV, ILIA

  DOI：——

  日期：——
• BADRAN, M. M.;EL-ANSARI, A. K.;EL-MELIGIE, S., REV. ROUM. CHIM., 35,(1990) N, C. 777-783
  作者：BADRAN, M. M.、EL-ANSARI, A. K.、EL-MELIGIE, S.

  DOI：——

  日期：——