2-(benzyloxy)-6-hydroxybenzoic acid | 71752-89-1

• 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: 2-(benzyloxy)-6-hydroxybenzoic acid
• 英文别名: 6-benzyloxysalicylic acid；2-Benzyloxy-6-hydroxybenzoesaeure；2-hydroxy-6-phenylmethoxybenzoic acid
• CAS: 71752-89-1
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: UDAGTZXHCWMZEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  2-(benzyloxy)-6-hydroxybenzoic acid 在 lithium aluminium tetrahydride 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 62.0h， 生成 3-Benzyloxy-2-hydroxymethyl-phenol
  参考文献：
  名称：

  Efficient and Selective Reduction Protocols of the 2,2-Dimethyl-1,3-benzodioxan-4-one Functional Group to Readily Provide Both Substituted Salicylaldehydes and 2-Hydroxybenzyl Alcohols

  摘要：

  Two complementary procedures have been developed that selectively allow for the synthesis of either substituted salicylaldehydes or the corresponding 2-hydroxylbenzyl alcohols upon treatment of the 2,2-dimethyl- 1,3-benzodioxan-4-one functional group with DIBAL-H or LAH, respectively.

  DOI：

  10.1021/jo0601664
• 作为产物：
  描述：

  2,6-二羟基苯甲酸 在 potassium hydrogencarbonate 、 三苯基膦 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(benzyloxy)-6-hydroxybenzoic acid
  参考文献：
  名称：

  γ-间苯二酸酯的选择性单O-烷基化

  摘要：

  描述了偶氮二羧酸二乙酯/三苯基膦用于γ-间苯二酸酯的选择性单-O-烷基化的用途。

  DOI：

  10.1016/s0040-4039(00)71469-9

文献信息

• Synthesis of oxa-analogues of zearalanone
  作者：Robert J. Bass、Bernard J. Banks、Michael R. G. Leeming、Michael Snarey

  DOI：10.1039/p19810000124

  日期：——

  The synthesis of macrocyclic lactones related to zearalanone is described. The reaction of salicylic acids with 1,9-dibromononane, 1,9-dichloro-5-oxanonane, and 1,9-dibromononan-5-one was used to prepare the corresponding lactones. Cyclisation of 2-(9-hydroxynonyloxy)benzoic acid, 4,6-dibenzyloxy-2-(9-hydroxynonyloxy)benzoic acid, and 4-benzyloxy-2-hydroxy-6-(9-hydroxy-5-oxodecyloxy)benzoic acid using

  描述了与泽拉丙酮有关的大环内酯的合成。将水杨酸与1，9-二溴mononane，1，9-二氯-5-氧杂壬烷和1，9-二溴一南-5-酮的反应用于制备相应的内酯。2-（9-羟基壬基氧基）苯甲酸，4,6-二苄氧基-2-（9-羟基壬基氧基）苯甲酸和4-苄氧基-2-羟基-6-（9-羟基-5-氧代癸氧基）苯甲酸的环化使用偶氮二羧酸二乙酯-三苯基膦以中等收率得到相应的内酯。
• Improved inhibition of the histone acetyltransferase PCAF by an anacardic acid derivative
  作者：Massimo Ghizzoni、André Boltjes、Chris de Graaf、Hidde J. Haisma、Frank J. Dekker

  DOI：10.1016/j.bmc.2010.06.089

  日期：2010.8

  Several lines of evidence indicate that histone acetyltransferases (HATs) are novel drug targets for treatment of diseases like, for example, cancer and inflammation. The natural product anacardic acid is a starting point for development of small molecule inhibitors of the histone acetyltransferase (HAT) p300/CBP associated factor (PCAF). In order to optimize the inhibitory potency, a binding model for PCAF inhibition by anacardic acid was proposed and new anacardic acid derivatives were designed. Ten new derivatives were synthesized using a novel synthetic route. One compound showed a twofold improved inhibitory potency for the PCAF HAT activity and a twofold improved inhibition of histone acetylation in HEP G2 cells. (C) 2010 Elsevier Ltd. All rights reserved.
• Design of HIV-1 integrase inhibitors targeting the catalytic domain as well as its interaction with LEDGF/p75: A scaffold hopping approach using salicylate and catechol groups
  作者：Xing Fan、Feng-Hua Zhang、Rasha I. Al-Safi、Li-Fan Zeng、Yumna Shabaik、Bikash Debnath、Tino W. Sanchez、Srinivas Odde、Nouri Neamati、Ya-Qiu Long

  DOI：10.1016/j.bmc.2011.06.058

  日期：2011.8

  HIV-1 integrase (IN) is a validated therapeutic target for antiviral drug design. However, the emergence of viral strains resistant to clinically studied IN inhibitors demands the discovery of novel inhibitors that are structurally as well mechanistically different. Herein, we describe the design and discovery of novel IN inhibitors targeting the catalytic domain as well as its interaction with LEDGF/p75, which is essential for the HIV-1 integration as an IN cofactor. By merging the pharmacophores of salicylate and catechol, the 2,3-dihydroxybenzamide (5a) was identified as a new scaffold to inhibit the strand transfer reaction efficiently. Further structural modifications on the 2,3-dihydroxybenzamide scaffold revealed that the heteroaromatic functionality attached on the carboxamide portion and the piperidin-1-ylsulfonyl substituted at the phenyl ring are beneficial for the activity, resulting in a low micromolar IN inhibitor (5p, IC(50) = 5 mu M) with more than 40-fold selectivity for the strand transfer over the 3'-processing reaction. More significantly, this active scaffold remarkably inhibited the interaction between IN and LEDGF/p75 cofactor. The prototype example, N-(cyclohexylmethyl)-2,3-dihydroxy-5-(piperidin-1-ylsulfonyl) benzamide (5u) inhibited the IN-LEDGF/p75 interaction with an IC(50) value of 8 mu M. Using molecular modeling, the mechanism of action was hypothesized to involve the chelation of the divalent metal ions inside the IN active site. Furthermore, the inhibitor of IN-LEDGF/p75 interaction was properly bound to the LEDGF/p75 binding site on IN. This work provides a new and efficient approach to evolve novel HIV-1 IN inhibitors from rational integration and optimization of previously reported inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.
• BASS R. J.; BANKS B. J.; SNAREY M., TETRAHEDRON LETT., 1980, 21, NO 8, 769-770
  作者：BASS R. J.、 BANKS B. J.、 SNAREY M.

  DOI：——

  日期：——
• TAKAHASHI HIROSHI; KUBOTA YUMIKO; LIN FANG; ONDA MASAYUKI, HETEROCYCLES, 24,(1986) N 3, 1099-1107
  作者：TAKAHASHI HIROSHI、 KUBOTA YUMIKO、 LIN FANG、 ONDA MASAYUKI

  DOI：——

  日期：——