(E)-6-chloro-3-styryl-4H-chromen-4-one | 1033328-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-6-chloro-3-styryl-4H-chromen-4-one
• 英文别名: (E)-6-chloro-3-styrylchromone；6-chloro-3-[(E)-2-phenylethenyl]chromen-4-one
• CAS: 1033328-39-0
• 化学式: C₁₇H₁₁ClO₂
• 分子量: 282.726
• InChiKey: XLMNQVNCVSEOOX-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-chloro-3-styryl-4H-chromen-4-one 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 以61%的产率得到trans-6-chloro-3-(3-phenyloxiran-2-yl)chromone
  参考文献：
  名称：

  3-苯乙烯基色酮的微波诱导合成及区域和立体选择性环氧化

  摘要：

  3-甲酰基色酮和苯丙二酸在醋酸钠载体上微波辅助无溶剂合成(E)-3-苯乙烯基色酮；该方法以中等至良好的收率和完全的非对映选择性提供苯乙烯基衍生物。(E)- 和 (Z)-3-styrylchromones 的高度区域选择性环氧化的协议已经详细说明。用二甲基二环氧乙烷处理烯烃导致形成具有完全非对映选择性的 3-(3-芳基环氧乙烷-2-基)色酮，而在碱性条件下用过氧化氢处理得到相应的 2,3-环氧-3-苯乙烯色酮作为只有产品。在手性非外消旋金鸡纳生物碱季铵盐存在下进行环氧化，合成富含对映体的 2，3-epoxy-3-styrylchromanones，但只有中等 ee 值。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejoc.200701081
• 作为产物：
  描述：

  苯乙酸 、 6-氯-3-甲酰基色酮 在 吡啶 、 potassium tert-butylate 作用下， 以52%的产率得到(E)-6-chloro-3-styryl-4H-chromen-4-one
  参考文献：
  名称：

  New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders

  摘要：

  Substituted (E)-3-styryl-4H-chromen-4-ones 1a-d, 3-[(1E,3E)-4-phenylbuta-1,3-dienyl]-4H-chromen-4-ones 2a-d, (E)-3-styryl-2H-chromenes 3a-d and 3-[(1E, 3E)-4-phenylbuta-1,3-dienyl]-2H-chromenes 4a-d were designed and synthesized to improve the anti-picornavirus activity of previously tested analogues. The new compounds were evaluated in vitro against human rhinovirus (HRV) serotypes 1B and 14 and enterovirus (EV) 71. All the compounds interfered with the replication of picornaviruses, although considerable differences were observed in the sensitivity of viruses to each compound. Generally, both HRVs were more susceptible than EV71 and their sensitivity was dependent upon the linker chain length as well as upon the oxidation state of the heterocyclic ring. (E)-3-Styryl-2H-chromene (3a) emerged as the most effective inhibitor of both HRVs showing IC50 values of 0.20 mu M and 1.38 mu M towards serotype 1B and 14, respectively. The potent activity was also coupled with low cytotoxicity resulting in high therapeutic indexes (250 and 36, respectively). Mechanism of action studies indicated that 3a, like structurally related compounds, behaves as a capsid binder interfering with the early stages of rhinovirus infection, probably at the adsorption and/or uncoating level. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.103

文献信息

• Syntheses of (E)- and (Z)-3-styrylchromones
  作者：Vera L. M. Silva、Artur M. S. Silva、Diana C. G. A. Pinto、José A. S. Cavaleiro、Attila Vasas、Tamás Patonay

  DOI：10.1007/s00706-008-0926-0

  日期：2008.11

  Several ( E )- and ( Z )-3-styrylchromones were prepared by two different methodologies, the Wittig reaction of chromone-3-carboxaldehyde with benzylic ylides and the Knoevenagel condensation of chromone-3-carboxaldehyde with phenylacetic acids in the presence of potassium tert -butoxide under microwave irradiation. The Knoevenagel reaction followed by a decarboxylation offered an efficient and diastereoselective

  通过两种不同的方法制备了几种（ E ）-和（ Z ）-3-苯乙烯基色酮，在钾存在下，色酮3-甲醛与苄基的 Wittig 反应以及色酮3-甲醛与苯乙酸的 Knoevenagel 缩合。 微波辐射下的 叔 丁醇盐。的 诺文葛耳 反应，然后脱羧提供了一个有效的和非对映选择性制备方法（ Ë ）-3-苯乙烯基色酮在较短的反应时间内。还证明了苯基乙酸也可以成功地被苯基丙二酸取代。通过NMR实验确定所有产物的立体化学。
• New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders
  作者：Cinzia Conti、Nicoletta Desideri

  DOI：10.1016/j.bmc.2010.06.103

  日期：2010.9

  Substituted (E)-3-styryl-4H-chromen-4-ones 1a-d, 3-[(1E,3E)-4-phenylbuta-1,3-dienyl]-4H-chromen-4-ones 2a-d, (E)-3-styryl-2H-chromenes 3a-d and 3-[(1E, 3E)-4-phenylbuta-1,3-dienyl]-2H-chromenes 4a-d were designed and synthesized to improve the anti-picornavirus activity of previously tested analogues. The new compounds were evaluated in vitro against human rhinovirus (HRV) serotypes 1B and 14 and enterovirus (EV) 71. All the compounds interfered with the replication of picornaviruses, although considerable differences were observed in the sensitivity of viruses to each compound. Generally, both HRVs were more susceptible than EV71 and their sensitivity was dependent upon the linker chain length as well as upon the oxidation state of the heterocyclic ring. (E)-3-Styryl-2H-chromene (3a) emerged as the most effective inhibitor of both HRVs showing IC50 values of 0.20 mu M and 1.38 mu M towards serotype 1B and 14, respectively. The potent activity was also coupled with low cytotoxicity resulting in high therapeutic indexes (250 and 36, respectively). Mechanism of action studies indicated that 3a, like structurally related compounds, behaves as a capsid binder interfering with the early stages of rhinovirus infection, probably at the adsorption and/or uncoating level. (C) 2010 Elsevier Ltd. All rights reserved.
• Microwave-Induced Synthesis and Regio- and Stereoselective Epoxidation of 3-Styrylchromones
  作者：Tamás Patonay、Attila Kiss-Szikszai、Vera M. L. Silva、Artur M. S. Silva、Diana C. G. A. Pinto、José A. S. Cavaleiro、József Jekő

  DOI：10.1002/ejoc.200701081

  日期：2008.4

  highly regioselective epoxidation of (E)- and (Z)-3-styrylchromones have been elaborated. Treatment of the alkenes with dimethyldioxirane led to the exclusive formation of 3-(3-aryloxiran-2-yl)chromones with complete diastereoselectivity, whereas treatment with hydrogen peroxide under alkaline conditions afforded the corresponding 2,3-epoxy-3-styrylchromanones as the only products. Epoxidation performed

  3-甲酰基色酮和苯丙二酸在醋酸钠载体上微波辅助无溶剂合成(E)-3-苯乙烯基色酮；该方法以中等至良好的收率和完全的非对映选择性提供苯乙烯基衍生物。(E)- 和 (Z)-3-styrylchromones 的高度区域选择性环氧化的协议已经详细说明。用二甲基二环氧乙烷处理烯烃导致形成具有完全非对映选择性的 3-(3-芳基环氧乙烷-2-基)色酮，而在碱性条件下用过氧化氢处理得到相应的 2,3-环氧-3-苯乙烯色酮作为只有产品。在手性非外消旋金鸡纳生物碱季铵盐存在下进行环氧化，合成富含对映体的 2，3-epoxy-3-styrylchromanones，但只有中等 ee 值。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)