[(4-chlorobenzyl)oxy]-4-(chloromethyl)-2H-chromen-2-one | 1270046-46-2

• 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
• 英文名称: [(4-chlorobenzyl)oxy]-4-(chloromethyl)-2H-chromen-2-one
• 英文别名: 4-(Chloromethyl)-7-[(4-chlorophenyl)methoxy]chromen-2-one
• CAS: 1270046-46-2
• 化学式: C₁₇H₁₂Cl₂O₃
• 分子量: 335.186
• InChiKey: MPQAJVGWLSCCSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-硫脲嘧啶 、 [(4-chlorobenzyl)oxy]-4-(chloromethyl)-2H-chromen-2-one 在 potassium carbonate 作用下， 生成
  参考文献：
  名称：

  Benzouracil–coumarin–arene conjugates as inhibiting agents for chikungunya virus

  摘要：

  Chikungunya virus (CHIKV) is an arbovirus that was first recognized in an epidemic form in East Africa in 1952-1953. The virus is primarily transmitted through mosquitoes and the resulting disease, chikungunya fever, is found in nearly 40 countries. Neither an effective vaccine nor a specific antiviral drug exists for treatments of chikungunya fever. Thus 22 new conjugated compounds of uracil-coumarin-arene were designed and synthesized as potential inhibiting agents. Their chemical structures were determined unambiguously by spectroscopic methods, including single-crystal X-ray diffraction crystallography. The three units in these conjugates were connected by specially designed -SCH2- and -OOSO2- joints. Five of these new conjugates were found to inhibit CHIKV in Vero cells with significant potency (ECK50 = 10.2-19.1 mu M) and showed low toxicity (CC50 = 75.2-178 mu M). The selective index values were 8.8-11.5 for three conjugates. By analysis of the data from the anti-viral assays, the structure-activity relationship is derived on the basis of the nature of the uracil, the functional groups attached to the arene, and the joints between the ring units. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.antiviral.2015.03.013
• 作为产物：
  描述：

  间苯二酚 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 丙酮 、 甲苯 为溶剂， 生成 [(4-chlorobenzyl)oxy]-4-(chloromethyl)-2H-chromen-2-one
  参考文献：
  名称：

  Benzouracil–coumarin–arene conjugates as inhibiting agents for chikungunya virus

  摘要：

  Chikungunya virus (CHIKV) is an arbovirus that was first recognized in an epidemic form in East Africa in 1952-1953. The virus is primarily transmitted through mosquitoes and the resulting disease, chikungunya fever, is found in nearly 40 countries. Neither an effective vaccine nor a specific antiviral drug exists for treatments of chikungunya fever. Thus 22 new conjugated compounds of uracil-coumarin-arene were designed and synthesized as potential inhibiting agents. Their chemical structures were determined unambiguously by spectroscopic methods, including single-crystal X-ray diffraction crystallography. The three units in these conjugates were connected by specially designed -SCH2- and -OOSO2- joints. Five of these new conjugates were found to inhibit CHIKV in Vero cells with significant potency (ECK50 = 10.2-19.1 mu M) and showed low toxicity (CC50 = 75.2-178 mu M). The selective index values were 8.8-11.5 for three conjugates. By analysis of the data from the anti-viral assays, the structure-activity relationship is derived on the basis of the nature of the uracil, the functional groups attached to the arene, and the joints between the ring units. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.antiviral.2015.03.013

文献信息

• Design, Synthesis, and Biological Evaluation of Imidazolyl Derivatives of 4,7-Disubstituted Coumarins as Aromatase Inhibitors Selective over 17-α-Hydroxylase/C17−20 Lyase
  作者：Angela Stefanachi、Angelo D. Favia、Orazio Nicolotti、Francesco Leonetti、Leonardo Pisani、Marco Catto、Christina Zimmer、Rolf W. Hartmann、Angelo Carotti

  DOI：10.1021/jm101120u

  日期：2011.3.24

  The design, synthesis, and biological evaluation of a series of new aromatase (AR, CYP19) inhibitors bearing an imidazole ring linked to a 7-substituted coumarin scaffold at position 4 (or 3) are reported. Many compounds exhibited an aromatase inhibitory potency in the nanomolar range along with a high selectivity over 17-α-hydroxylase/C17−20 lyase (CYP17). The most potent AR inhibitor was the 7-(3

  报道了一系列新的芳香酶（AR，CYP19）抑制剂的设计，合成和生物学评估，这些抑制剂带有与7位取代的香豆素骨架连接的4位（或3位）咪唑环。许多化合物在纳摩尔浓度范围内均显示出芳香化酶抑制潜能，并且对17-α-羟化酶/ C17-20裂解酶（CYP17）具有较高的选择性。最有效的AR抑制剂是7-（3,4-二氟苯氧基）-4-咪唑基甲基香豆素24，IC 50 = 47 nM。在一定数量的香豆素衍生物上的对接模拟可以识别驱动结合的最重要的相互作用，并清楚地表明香豆素和紧密相关的杂环分子支架的适当结构修饰的允许和不允许的区域。
• Benzouracil–coumarin–arene conjugates as inhibiting agents for chikungunya virus
  作者：Jih Ru Hwu、Mohit Kapoor、Shwu-Chen Tsay、Chun-Cheng Lin、Kuo Chu Hwang、Jia-Cherng Horng、I-Chia Chen、Fa-Kuen Shieh、Pieter Leyssen、Johan Neyts

  DOI：10.1016/j.antiviral.2015.03.013

  日期：2015.6

  Chikungunya virus (CHIKV) is an arbovirus that was first recognized in an epidemic form in East Africa in 1952-1953. The virus is primarily transmitted through mosquitoes and the resulting disease, chikungunya fever, is found in nearly 40 countries. Neither an effective vaccine nor a specific antiviral drug exists for treatments of chikungunya fever. Thus 22 new conjugated compounds of uracil-coumarin-arene were designed and synthesized as potential inhibiting agents. Their chemical structures were determined unambiguously by spectroscopic methods, including single-crystal X-ray diffraction crystallography. The three units in these conjugates were connected by specially designed -SCH2- and -OOSO2- joints. Five of these new conjugates were found to inhibit CHIKV in Vero cells with significant potency (ECK50 = 10.2-19.1 mu M) and showed low toxicity (CC50 = 75.2-178 mu M). The selective index values were 8.8-11.5 for three conjugates. By analysis of the data from the anti-viral assays, the structure-activity relationship is derived on the basis of the nature of the uracil, the functional groups attached to the arene, and the joints between the ring units. (C) 2015 Elsevier B.V. All rights reserved.