5,5'-dibromo-3,3'-dicarboxy-2,2'-dihydroxydiphenylmethane | 35232-55-4

• 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: 5,5'-dibromo-3,3'-dicarboxy-2,2'-dihydroxydiphenylmethane
• 英文别名: Benzoic acid, 3,3'-methylenebis[5-bromo-2-hydroxy-；5-bromo-3-[(5-bromo-3-carboxy-2-hydroxyphenyl)methyl]-2-hydroxybenzoic acid
• CAS: 35232-55-4
• 化学式: C₁₅H₁₀Br₂O₆
• 分子量: 446.049
• InChiKey: LWQWHZWYCPLAKB-UHFFFAOYSA-N

物化性质

• 熔点：
  281-286 °C (decomp)
• 沸点：
  612.9±55.0 °C(Predicted)
• 密度：
  1.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5'-dibromo-3,3'-dicarboxy-2,2'-dihydroxydiphenylmethane 在 氢氧化钾 、 锌 作用下， 生成 1-[5-(2-羟基乙基)硫代]-4-硝基-2-噻吩]乙基-1-酮
  参考文献：
  名称：

  4,11,18,25-四氯[1 4 ] metacyclophane-7,14,21,28-tetroi的合成，叶绿素的结构类似物†

  摘要：

  描述了标题化合物的合成。所制备的某些化合物在体外表现出抗微生物活性。简要讨论了结构与活动的关系。

  DOI：

  10.1002/hlca.19820650411
• 作为产物：
  描述：

  5,5'-dibromo-3,3'-dicarbomethoxy-2,2'-dihydroxydiphenylmethane 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.67h， 以97%的产率得到5,5'-dibromo-3,3'-dicarboxy-2,2'-dihydroxydiphenylmethane
  参考文献：
  名称：

  单和二水杨酸衍生物：PTP1B抑制剂可作为潜在的抗肥胖药。

  摘要：

  合成了一系列包含一个或两个水杨酸部分的化合物，并研究了其抑制PTP1B磷酸水解酶活性的功效。一些亚甲基二水杨酸衍生物是PTP1B的有效抑制剂。在这些衍生物中，3c对TC-PTP表现出约14倍的选择性，并在小鼠模型中测试了该化合物预防饮食引起的肥胖的功效。它有效地抑制了体重和脂肪的增加，而没有任何明显的毒性作用。该化合物还可以防止血浆甘油三酸酯，胆固醇和非酯化脂肪酸浓度的增加。因此，将其治疗潜力扩展到其他相关的代谢性疾病，例如高脂血症和高胆固醇血症。

  DOI：

  10.1016/j.bmc.2007.07.010

文献信息

• The Synthesis of 4,11,18,25-Tetrachloro [14]metacyclophane-7,14,21,28-tetroi, Structural Analogues of Phloroglucides
  作者：Ali A. Moshfegh、Rashid Badri、Massoud Hojjatie、Mehrangiz Kaviani、Basirat Naderi、Aboul H. Nazmi、Merrikh Ramezanian、Bizhan Roozpeikar、Gholam H. Haakimelahi

  DOI：10.1002/hlca.19820650411

  日期：1982.6.16

  The synthesis of the title compounds is described. Some of the compounds prepared exhibited antimicrobial activity in vitro. Structure-activity relationship is briefly discussed.

  描述了标题化合物的合成。所制备的某些化合物在体外表现出抗微生物活性。简要讨论了结构与活动的关系。
• Synthesis and Biological Evaluation of Certain Alkenyldiarylmethanes as Anti-HIV-1 Agents Which Act as Non-Nucleoside Reverse Transcriptase Inhibitors
  作者：Mark Cushman、W. Marek Golebiewski、Lisa Graham、Jim A. Turpin、William G. Rice、Valerie Fliakas-Boltz、Robert W. Buckheit

  DOI：10.1021/jm960082v

  日期：1996.1.1

  Several novel alkenyldiarylmethane (ADAM) non-nucleoside HIV-1 reverse transcriptase inhibitors were synthesized. The most potent of these proved to be 3',3''-dibromo-4',4 ''-dimethoxy-5',5 ''-bis(methoxycarbonyl)-1,1-diphenyl-1-heptene (8). ADAM 8 inhibited the cytopathic effect of HIV-1 in CEM cell culture with an EC(50) value of 7.1 mu M and was active against an array of laboratory strains of HIV-1 in CEM-SS and MT-4 cells, but was inactive as an inhibitor of HIV-2. In common with the other known non-nucleoside reverse transcriptase inhibitors, ADAM 8 was an effective inhibitor of HIV-1 reverse transcriptase (IC50 1 mu M) with poly(rC). oligo(dG), but not with poly(rA). oligo(dT), as the template/primer. ADAM 8 was inactive against HIV-1 reverse transcriptases containing non-nucleoside reverse transcriptase inhibitor resistance mutations at residues 101, 106, 108, 139, 181, 188, and 236, while it remained active against enzymes with mutations at residues 74, 98, 100, 103, and at 103/181. An AZT-resistant virus having four mutations in reverse transcriptase was more sensitive to inhibition by ADAM 8 than the wild-type HIV-1. In addition, ADAM 8 displayed synergistic activity with AZT, but lacked synergy with ddI. ADAM 8 or a structurally related analog may therefore be useful as an antiviral agent in combination with AZT or with other NNRTIs that are made ineffective by mutations at residues which do not confer resistance to ADAM 8.
• Lithiation of polyhydric compounds. Salicylic acids
  作者：M. Carmen Rotger、Antoni Costa、Jose M. Saa

  DOI：10.1021/jo00067a048

  日期：1993.7

  Polylithiated derivatives of salicylic and oligosalicylic acids can be generated by means of the halogen-to-metal exchange reaction. Dehydrobromination and other byproducts can be kept to a minimum by working with the preformed lithium salts which are soluble in THF. Even base sensitive salicylic acids such as 6-bromolasalocid acid can be functionalized under these conditions.
• CUSHMAN, MARK;KANAMATHAREDDY, SUSEELA;DE, CLERCQ ERIK;SCHOLS, DOMINIQUE;G+, J. MED. CHEM., 34,(1991) N, C. 337-342
  作者：CUSHMAN, MARK、KANAMATHAREDDY, SUSEELA、DE, CLERCQ ERIK、SCHOLS, DOMINIQUE、G+

  DOI：——

  日期：——
• Synthesis and anti-HIV activities of low molecular weight aurintricarboxylic acid fragments and related compounds
  作者：Mark Cushman、Suseela Kanamathareddy、Erik De Clercq、Dominique Schols、Mark E. Goldman、Julie A. Bowen

  DOI：10.1021/jm00105a053

  日期：1991.1

  Several compounds corresponding to fragments of the schematic representation of the polymeric structure of aurintricarboxylic acid (ATA) have been prepared and tested for prevention of the cytopathic effect of HIV-1 and HIV-2 in MT-4 cell culture and HIV-1 in CEM cell culture. Both the triphenylcarbinol 3 as well as the triphenylmethane 5 were found to afford protection against the cytopathogenicity of HIV-2 in MT-4 cells and HIV-1 in CEM cells, but they were inactive against HIV-1 in MT-4 cells. Both substances were also found to inhibit syncytium formation when MOLT-4 cells were cocultured with HIV-2-infected HUT-78 cells, but were inactive in this assay against HIV-1-infected cells. When observed, the activity is generally moderate in degree of protection and requires concentrations in the 10(-4) molar range. In contrast to ATA, both of these substances were inactive when tested for prevention of the binding of the OKT4A monoclonal antibody to the CD4 receptor and also for inhibition of HIV-1 reverse transcriptase. These substances therefore appear act by a mechanism that is distinct from that of polymeric ATA. Several active and inactive structural analogues of 3 and 5 were also synthesized. The anti-HIV activity in this series seems to depend on the presence of anionic carboxylate groups, since the methyl esters 4, 6, and 12 were uniformly inactive. The diphenylmethanes 8, 14, 18, and 19 also reproducibly inhibited the cytopathic effect of HIV-1 in CEM cell culture.