3,4-bis(methoxycarbonyloxy)-phenylacetic acid | 222320-70-9

• 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: 3,4-bis(methoxycarbonyloxy)-phenylacetic acid
• 英文别名: 3,4-dimethoxycarbonylphenylacetic acid；2-[3,4-Bis(methoxycarbonyloxy)phenyl]acetic acid
• CAS: 222320-70-9
• 化学式: C₁₂H₁₂O₈
• 分子量: 284.222
• InChiKey: BDYSIQLRJFMXLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4-bis(methoxycarbonyloxy)-phenylacetic acid 在 草酰氯 作用下， 反应 1.0h， 生成 Carbonic acid 4-chlorocarbonylmethyl-2-methoxycarbonyloxy-phenyl ester methyl ester
  参考文献：
  名称：

  Novel HIV integrase inhibitors and HIV therapy based on drug combinations including integrase inhibitors

  摘要：

  本发明包括一组新颖的化合物，已被证明能够在体外强力且选择性地抑制HIV整合酶（IN）活性，并在非毒性浓度下有效抑制活体培养细胞中的HIV复制。所披露的新颖化合物包括2,3-二（3,4-二羟基-二羟基二羟基肉桂酰）-L-酒石酸，2,3-二（3,4-二羟基苯甲酰）-L-酒石酸，2,3-二（3,4-二羟基苯乙酰）-L-酒石酸，2,3-二（3,4,5-三羟基苯甲酰）-L-酒石酸，2,3-二咖啡酰二氨基丙酸，1,2-二咖啡酰-L-甘油酸，双-3,4-二咖啡酰二氨基苯甲酸，二-3,4-二羟基苯乙烯琥珀酸，二-3,4-二羟基二羟基苯乙烯琥珀酸，2,3-二咖啡酰-L-丝氨酸，双咖啡酰-L-异丝氨酸和1,4-二咖啡酰-L-赖氨酸。对整合酶抑制剂与2′,3′-二脱氧胞苷、阿司匹林和奈非那韦（蛋白酶抑制剂）的测试表明，对逆转录酶抑制剂耐药病毒具有强大的协同作用。将整合酶抑制剂添加到联合药物疗法中的潜在益处是显著的。

  公开号：

  US20050049242A1
• 作为产物：
  描述：

  3,4-二羟基苯乙酸 、 氯甲酸甲酯 在 盐酸 作用下， 以 sodium hydroxide 为溶剂， 生成 3,4-bis(methoxycarbonyloxy)-phenylacetic acid
  参考文献：
  名称：

  Phenolic acid amides of hydroxy-substituted benzylamines

  摘要：

  本发明涉及一种公式I的羟基取代苄胺的特定酚酸酰胺，其为抗氧化剂或自由基清除剂，特别是在化妆品或皮肤学领域中，以及在食品和化妆品和皮肤学组合物中包含这些酚酸酰胺的用途的制备方法。

  公开号：

  US06117365A1

文献信息

• Novel HIV integrase inhibitors and HIV therapy based on drug combinations including integrase inhibitors
  申请人：Robinson W. Edward

  公开号：US20050049242A1

  公开（公告）日：2005-03-03

  The present invention includes a group of novel compounds that are demonstrated to potently and selectively inhibit HIV integrase (IN) activity in vitro and to potently inhibit HIV replication in live, cultured cells at non-toxic concentrations. The novel compounds disclosed include 2,3-di(3,4-dihydroxy-dihydroxydihydrocinnamoyl)-L-tartaric acid, 2,3-di-(3,4-dihydroxybenzoyl)-L-tartaric acid, 2,3-di-(3,4-dihydroxyphenylacetyl)-L-tartaric acid, 2,3-di-(3,4,5-trihydroxybenzoyl-L-tartaric acid, 2,3-dicaffeoyldiamidopropionic acid, 1,2,-dicaffeoyl-L-glyceric acid, bis,-3,4-dicaffeoyldiamidobenzoic acid, di-3,4-dihydroxybenzylidene succinic acid, di-3,4-dihydrodihydroxybenzylidine succinic acid, 2,3-dicaffeoyl-L-serine, bis-dicaffeoyl-L-isoserine and 1,4-dicaffeoyl-L-lysine. Tests of integrase inhibitors with 2′,3′-dideoxycytidine, zidovudine and nelfinavir (protease inhibitor) indicated a potent synergy against reverse transcriptase inhibitor resistant virus. The potential benefit from the addition of integrase inhibitors to combination drug therapies is significant.

  本发明包括一组新颖的化合物，已被证明能够在体外强力且选择性地抑制HIV整合酶（IN）活性，并在非毒性浓度下有效抑制活体培养细胞中的HIV复制。所披露的新颖化合物包括2,3-二（3,4-二羟基-二羟基二羟基肉桂酰）-L-酒石酸，2,3-二（3,4-二羟基苯甲酰）-L-酒石酸，2,3-二（3,4-二羟基苯乙酰）-L-酒石酸，2,3-二（3,4,5-三羟基苯甲酰）-L-酒石酸，2,3-二咖啡酰二氨基丙酸，1,2-二咖啡酰-L-甘油酸，双-3,4-二咖啡酰二氨基苯甲酸，二-3,4-二羟基苯乙烯琥珀酸，二-3,4-二羟基二羟基苯乙烯琥珀酸，2,3-二咖啡酰-L-丝氨酸，双咖啡酰-L-异丝氨酸和1,4-二咖啡酰-L-赖氨酸。对整合酶抑制剂与2′,3′-二脱氧胞苷、阿司匹林和奈非那韦（蛋白酶抑制剂）的测试表明，对逆转录酶抑制剂耐药病毒具有强大的协同作用。将整合酶抑制剂添加到联合药物疗法中的潜在益处是显著的。
• Phenolic acid amides of hydroxy-substituted benzylamines
  申请人：Haarmann & Reimer GmbH

  公开号：US06117365A1

  公开（公告）日：2000-09-12

  The invention relates to specific phenolic acid amides of hydroxy-substituted benzylamines of the formula I ##STR1## to a process for their preparation and to their use as antioxidants or as free-radical scavengers, in particular in the cosmetic or dermatological field, in foods and cosmetic and dermatological compositions comprising these phenolic acid amides.

  本发明涉及一种公式I的羟基取代苄胺的特定酚酸酰胺，其为抗氧化剂或自由基清除剂，特别是在化妆品或皮肤学领域中，以及在食品和化妆品和皮肤学组合物中包含这些酚酸酰胺的用途的制备方法。
• Phenolsäureamide hydroxysubstituierter Benzylamine
  申请人：HAARMANN & REIMER GMBH

  公开号：EP0900781B1

  公开（公告）日：2002-03-20
• US6117365A
  申请人：——

  公开号：US6117365A

  公开（公告）日：2000-09-12
• Structure−Activity Relationships:  Analogues of the Dicaffeoylquinic and Dicaffeoyltartaric Acids as Potent Inhibitors of Human Immunodeficiency Virus Type 1 Integrase and Replication
  作者：Peter J. King、Guoxiang Ma、Wenfang Miao、Qi Jia、Brenda R. McDougall、Manfred G. Reinecke、Chris Cornell、Jean Kuan、Tracey R. Kim、W. Edward Robinson

  DOI：10.1021/jm9804735

  日期：1999.2.1

  The dicaffeoylquinic acids (DCQAs) and dicaffeoyltartaric acids (DCTAs) are potent and selective inhibitors of human immunodeficiency virus type 1 (HIV-1) integrase. They also inhibit HIV-1 replication at nontoxic concentrations; Since integrase is an excellent target for anti-HIV therapy, structure-activity relationships were employed to synthesize compounds with: (1) improved potency against HIV-1 integrase, (2) improved anti-HIV effect in tissue culture, and (3) increased selectivity as indicated by low cellular toxicity. Thirty-four analogues of the DCTAs and DCQAs were synthesized and tested for cell toxicity, anti-HIV activity, and inhibition of HIV-1 integrase. Seventeen of the 34 analogues had potent activity against HIV-1 integrase ranging from 0.07 to >10 mu M. Seventeen analogues that were synthesized or purchased had no inhibitory activity against integrase at concentrations of 25 mu M. Of the biologically active analogues, 7 of the 17 inhibited HIV replication at nontoxic concentrations. The most potent compounds were D-chicoric acid, meso-chicoric acid, bis(3,4-dihydroxydihydrocinnamoyl)-L-tartaric acid, digalloyl-L-tartaric acid, bis(3,4-dihydroxybenzoyl)-L-tartaric acid, dicaffeoylglyceric acid, and bis(3,4-dihydroxyphenylacetyl)-L-tartaric acid. Anti-HIV activity of the active compounds in tissue culture ranged from 35 to 0.66 mu M. Structure-activity relationships demonstrated that biscatechol moieties were absolutely required for inhibition of integrase, while at least one free carboxyl group was required for anti-HIV activity. These data demonstrate that analogues of the DCTAs and the DCQAs can be synthesized which have improved activity against HIV integrase.