3,3'-dicarbomethoxy-5,5'-dichloro-4,4'-dihydroxydiphenylmethane | 397843-09-3

• 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: 3,3'-dicarbomethoxy-5,5'-dichloro-4,4'-dihydroxydiphenylmethane
• 英文别名: Methyl 3-chloro-5-[(3-chloro-4-hydroxy-5-methoxycarbonylphenyl)methyl]-2-hydroxybenzoate
• CAS: 397843-09-3
• 化学式: C₁₇H₁₄Cl₂O₆
• 分子量: 385.201
• InChiKey: ISUSCMNPHFNYTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3'-dicarbomethoxy-5,5'-dichloro-4,4'-dihydroxydiphenylmethane 在 吡啶 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 氢氧化钾 、 tetrachlorobis(tetrahydrofuran)titanium(IV) 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙酸酐 为溶剂， 反应 84.0h， 生成 24-[bis[5'-chloro-4'-hydroxy-3'-(carboxy)phenyl]methylene]-3α,7α,12α-trihydroxycholane
  参考文献：
  名称：

  Synthesis and anti-HIV activity of a bile acid analog of cosalane

  摘要：

  Cosalane is a novel anti-HIV agent that inhibits the attachment of gp120 to CD4. The therapeutic potential of cosalane is limited by poor oral absorption. In an attempt to target the ileal bile acid transporter and thus facilitate oral bioavailability, a cosalane analog was synthesized in which the disalicylmethane pharmacophore is attached to a bile acid through a linker chain appended to C-17 of the steroid nucleus. The resulting bile acid analog of cosalane, retained antiviral activity vs. HIV-1(IIIB) and HIV-2(ROD) in MT-4 cells, but was less potent than cosalane. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00955-3
• 作为产物：
  描述：

  3,3'-dicarboxy-5,5'-dichloro-4,4'-dihydroxydiphenylmethane 、 三甲基硅烷化重氮甲烷 以 甲醇 、 正己烷 、 苯 为溶剂， 反应 10.0h， 以45%的产率得到3,3'-dicarbomethoxy-5,5'-dichloro-4,4'-dihydroxydiphenylmethane
  参考文献：
  名称：

  Synthesis and anti-HIV activity of a bile acid analog of cosalane

  摘要：

  Cosalane is a novel anti-HIV agent that inhibits the attachment of gp120 to CD4. The therapeutic potential of cosalane is limited by poor oral absorption. In an attempt to target the ileal bile acid transporter and thus facilitate oral bioavailability, a cosalane analog was synthesized in which the disalicylmethane pharmacophore is attached to a bile acid through a linker chain appended to C-17 of the steroid nucleus. The resulting bile acid analog of cosalane, retained antiviral activity vs. HIV-1(IIIB) and HIV-2(ROD) in MT-4 cells, but was less potent than cosalane. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00955-3

文献信息

• Methylenedisalicylic acid derivatives: New PTP1B inhibitors that confer resistance to diet-induced obesity
  作者：Suja Shrestha、Bharat Raj Bhattarai、Kyung Ja Chang、Keun-Hyeung Lee、Hyeongjin Cho

  DOI：10.1016/j.bmcl.2007.02.069

  日期：2007.5

  Methylenedisalicylic acid derivatives were synthesized and their inhibitory activities against protein tyrosine phosphalases (PTPases) examined. Two of the compounds, 8 and 9, showed K-i values of 9.4 and 6.3 mu M against PTP I B, 4- and 7-fold lower values compared to those against TC-PTP. They were reversible and slow-binding inhibitors against PTP I B. When compound 8 was fed to a mouse model, the weight gain and adipocyte fat storage induced by a high-fat-diet were significantly suppressed. (c) 2007 Elsevier Ltd. All rights reserved.
• Investigation of the alkenyldiarylmethane non-nucleoside reverse transcriptase inhibitors as potential cAMP phosphodiesterase-4B2 inhibitors
  作者：Matthew D. Cullen、York-Fong Cheung、Miles D. Houslay、Tracy L. Hartman、Karen M. Watson、Robert W. Buckheit、Christophe Pannecouque、Erik De Clercq、Mark Cushman

  DOI：10.1016/j.bmcl.2007.12.015

  日期：2008.2

  The alkenyldiarylmethanes ( ADAMs) are currently being investigated as non- nucleoside HIV- 1 reverse transcriptase inhibitors ( NNRTIs) of potential value in the treatment of HIV infection and AIDS. During the course of these studies, a number of ADAM analogues have been identified that protect HIV- infected cells from the cytopathic effects of the virus by an unknown, HIV- 1 RT- independent mechanism. Since the phosphodiesterase 4 family is required for HIV infection, the effect of various ADAMs on the activity of PDE4B2 was investigated in an effort to determine if the ADAMs could possibly be targeting phosphodiesterases. Six compounds representative of the ADAM class were tested for inhibition of cAMP hydrolysis by PDE4B2 enzymatic activity. Four ADAMs were found to be weak inhibitors of PDE4B2 and two of them were inactive. The experimental results are consistent with an antiviral mechanism that does not include inhibition of PDE4 isoforms. (C) 2007 Elsevier Ltd. All rights reserved.