3-[(3-Phenylmethoxyphenyl)methylidene]chromen-4-one | 556042-41-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 3-[(3-Phenylmethoxyphenyl)methylidene]chromen-4-one
• CAS: 556042-41-2
• 化学式: C₂₃H₁₈O₃
• 分子量: 342.394
• InChiKey: QDDXJZRLQPYMLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  3-[(3-Phenylmethoxyphenyl)methylidene]chromen-4-one 在 盐酸 、 sodium tetrahydroborate 、 水 、 氢气 、 sodium hexamethyldisilazane 、 potassium carbonate 、 钯 、 (+)-8,8-二氯樟脑磺哑嗪 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c]chromene-6a,9-diol
  参考文献：
  名称：

  Synthesis and biological evaluation of deoxy-hematoxylin derivatives as a novel class of anti-HIV-1 agents

  摘要：

  SAR studies for the exploration a novel class of anti-human immunodeficiency virus type 1 (HIV-1) agents based on the hematoxylin structure (1) are described. The systematic deoxygenations of 1 including asymmetric synthesis were conducted to obtain a compound showing high potencies for inhibiting the nuclear import and viral replication as anti-HIV-1 agent. Among all, C-3-deoxygenated analog 16 exhibited most promising biological activities as anti-HIV-1 agent such as lower cytotoxicity (16: 1; >80:40 mu M), stronger inhibition of nuclear import (0.5:1.3 mu M), and viral replication in HIV-1-infected TZM-bl cells (24.6:100 mu M), human peripheral blood mononuclear cells (PMBCs) (30.1 mu M: toxic). Different spectra of inhibitory activities against infected three healthy humans macrophages with high (donor A) and low (donor B and C) amounts of virus were also observed. Thus 16 showed 10-times stronger activity than 1 (16: 1; 0.1:<1.0 mu M) in the case of A, while 16 and 1 showed comparable activities in the cases of B and C (>0.01 and >0.001 mu M). The comparison of the inhibition of viral p24 antigen production was clearly indicated that compound 16 is at least twofold more potent anti-viral activity than 1. Thus, structures and actions of deoxy analogs particularly 16 could provide valuable information for the development of a novel class of anti-HIV-1 agents. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.06.066
• 作为产物：
  描述：

  2,3-二氢苯并吡喃-4-酮 、 3-苄氧基苯甲醛 在 盐酸 作用下， 以 乙醇 为溶剂， 以76%的产率得到3-[(3-Phenylmethoxyphenyl)methylidene]chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of deoxy-hematoxylin derivatives as a novel class of anti-HIV-1 agents

  摘要：

  SAR studies for the exploration a novel class of anti-human immunodeficiency virus type 1 (HIV-1) agents based on the hematoxylin structure (1) are described. The systematic deoxygenations of 1 including asymmetric synthesis were conducted to obtain a compound showing high potencies for inhibiting the nuclear import and viral replication as anti-HIV-1 agent. Among all, C-3-deoxygenated analog 16 exhibited most promising biological activities as anti-HIV-1 agent such as lower cytotoxicity (16: 1; >80:40 mu M), stronger inhibition of nuclear import (0.5:1.3 mu M), and viral replication in HIV-1-infected TZM-bl cells (24.6:100 mu M), human peripheral blood mononuclear cells (PMBCs) (30.1 mu M: toxic). Different spectra of inhibitory activities against infected three healthy humans macrophages with high (donor A) and low (donor B and C) amounts of virus were also observed. Thus 16 showed 10-times stronger activity than 1 (16: 1; 0.1:<1.0 mu M) in the case of A, while 16 and 1 showed comparable activities in the cases of B and C (>0.01 and >0.001 mu M). The comparison of the inhibition of viral p24 antigen production was clearly indicated that compound 16 is at least twofold more potent anti-viral activity than 1. Thus, structures and actions of deoxy analogs particularly 16 could provide valuable information for the development of a novel class of anti-HIV-1 agents. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.06.066

文献信息

• Synthesis and biological evaluation of deoxy-hematoxylin derivatives as a novel class of anti-HIV-1 agents
  作者：Hideki Ishii、Hiroko Koyama、Kyoji Hagiwara、Tomoyuki Miura、Guangai Xue、Yoshie Hashimoto、Genta Kitahara、Yoko Aida、Masaaki Suzuki

  DOI：10.1016/j.bmcl.2011.06.066

  日期：2012.2

  SAR studies for the exploration a novel class of anti-human immunodeficiency virus type 1 (HIV-1) agents based on the hematoxylin structure (1) are described. The systematic deoxygenations of 1 including asymmetric synthesis were conducted to obtain a compound showing high potencies for inhibiting the nuclear import and viral replication as anti-HIV-1 agent. Among all, C-3-deoxygenated analog 16 exhibited most promising biological activities as anti-HIV-1 agent such as lower cytotoxicity (16: 1; >80:40 mu M), stronger inhibition of nuclear import (0.5:1.3 mu M), and viral replication in HIV-1-infected TZM-bl cells (24.6:100 mu M), human peripheral blood mononuclear cells (PMBCs) (30.1 mu M: toxic). Different spectra of inhibitory activities against infected three healthy humans macrophages with high (donor A) and low (donor B and C) amounts of virus were also observed. Thus 16 showed 10-times stronger activity than 1 (16: 1; 0.1:<1.0 mu M) in the case of A, while 16 and 1 showed comparable activities in the cases of B and C (>0.01 and >0.001 mu M). The comparison of the inhibition of viral p24 antigen production was clearly indicated that compound 16 is at least twofold more potent anti-viral activity than 1. Thus, structures and actions of deoxy analogs particularly 16 could provide valuable information for the development of a novel class of anti-HIV-1 agents. (C) 2011 Published by Elsevier Ltd.