methyl 2-(3-hydroxypropoxy)benzoate | 56717-53-4

• 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: methyl 2-(3-hydroxypropoxy)benzoate
• 英文别名: 2-(3-Hydroxypropoxy)benzoic acid methyl ester
• CAS: 56717-53-4
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: WVYPTZOAWPFYQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-hydroxypropoxy)benzoate 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 o-(3-hydroxypropoxy)benzoic acid
  参考文献：
  名称：

  Computer-Guided Design, Synthesis, and Protein Kinase C Affinity of a New Salicylate-Based Class of Bryostatin Analogs

  摘要：

  Bryostatin 1 is in clinical trials for the treatment of cancer and alzheimer disease and is a candidate for a first in class approach to HIV/AIDS eradication. It is neither readily available nor optimally suited for clinical use. Using a funciton oriented synthesis strategy, a new class of bryostatin inspired analog was designed with a simplified salicylate-derived subunit, enabling step economical synthesis (23 total steps) of agents exhibiting bryostatin like affinity to protein kinase C (PKC).

  DOI：

  10.1021/ol502491f
• 作为产物：
  描述：

  3-溴-1-丙醇 、 水杨酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以50%的产率得到methyl 2-(3-hydroxypropoxy)benzoate
  参考文献：
  名称：

  [EN] SUBSTITUTED CHROMANE-8-CARBOXAMIDE COMPOUNDS AND ANALOGUES THEREOF, AND METHODS USING SAME
  [FR] COMPOSÉS DE CHROMANE-8-CARBOXAMIDE SUBSTITUÉS ET ANALOGUES DE CEUX-CI, ET PROCÉDÉS LES UTILISANT

  摘要：

  本发明包括新颖的取代双环（例如4-取代-色苷-8-羧酰胺化合物），以及包含这些化合物的组合物，可用于治疗或预防患者体内的乙型肝炎病毒（HBV）感染。在某些实施例中，本发明的化合物和组合物是衣壳抑制剂。

  公开号：

  WO2018052967A1

文献信息

• Towards 20,20-difluorinated bryostatin: synthesis and biological evaluation of C17,C27-fragments
  作者：Paul R. Mears、Steven Hoekman、Claire E. Rye、Fiona P. Bailey、Dominic P. Byrne、Patrick A. Eyers、Eric J. Thomas

  DOI：10.1039/c8ob03152e

  日期：——

  Bryostatins with modified C17–C27 fragments have not been widely studied. The synthesis of 20,20-difluorinated analogues was therefore investigated. Such substitution would inhibit dehydration involving the C19-hydroxyl group and stabilise the ring-closed hemiacetal tautomers. Following preliminary studies, allyldifluorination was used to prepare difluorinated alkenols. Oxidation followed by stereoselective

  具有修饰的 C17-C27 片段的苔藓抑素尚未得到广泛研究。因此研究了 20,20-二氟化类似物的合成。这种取代将抑制涉及 C19-羟基的脱水并稳定闭环半缩醛互变异构体。经过初步研究，烯丙基二氟化用于制备二氟化烯醇。氧化后生成的 α,α-二氟化酮的立体选择性 Wittig 反应得到 ( E)-α,β-不饱和酯，用于完成对应于 20,20-二氟化苔藓抑素的 C17-C27 片段的 2-羟基四氢吡喃的合成。这些化合物显示出与蛋白激酶 Cα 同工酶的适度结合。还尝试合成大环20,20-二氟化类似物。在初步研究期间，使用 2-烷基-3-溴-1,1-二氟丙烯进行烯丙基二氟化。
• Substituted chromane-8-carboxamide compounds and analogues thereof, and methods using same
  申请人：ARBUTUS BIOPHARMA CORPORATION

  公开号：US11001564B2

  公开（公告）日：2021-05-11

  The present invention includes novel substituted bicyclic (such as 4-substituted-chromane-8-carboxamide compounds), and compositions comprising the same, that can be used to treat or prevent hepatitis B virus (HBV) infections in a patient. In certain embodiments, the compounds and compositions of the invention are capsid inhibitors.

  本发明包括可用于治疗或预防患者乙型肝炎病毒（HBV）感染的新型取代双环化合物（如 4-取代-苯并吡喃-8-甲酰胺化合物）以及包含这些化合物的组合物。在某些实施方案中，本发明的化合物和组合物是噬菌体抑制剂。
• Evaluation of Chromane-Based Bryostatin Analogues Prepared via Hydrogen-Mediated C–C Bond Formation: Potency Does Not Confer Bryostatin-like Biology
  作者：John M. Ketcham、Ivan Volchkov、Te-Yu Chen、Peter M. Blumberg、Noemi Kedei、Nancy E. Lewin、Michael J. Krische

  DOI：10.1021/jacs.6b08695

  日期：2016.10.12

  The synthesis and biological evaluation of chromane-containing bryostatin analogues WN-2 WN-7 and the previously reported salicylate-based analogue WN-8 are described. Analogues WN-2 WN-7 are prepared through convergent assembly of the chromane-containing fragment B-I with the "binding domain" fragment A-I or its C26-des-methyl congener, fragment A-II. The synthesis of fragment B-I features enantioselective double C-H allylation of 1,3-propanediol to form the C-2-symmetric diol 3 and Heck cyclization of bromo-diene 5 to form the chromane core. The synthesis of salicylate WN-8 is accomplished through the union of fragments A-III and B-II. The highest binding affinities for PKC alpha are observed for the C26-des-methyl analogues WN-3 (K-i = 63.9 nM) and WN-7 (K-i = 63.1 nM). All analogues, WN-2 WN-8, inhibited growth of Toledo cells, with the most potent analogue being WN-7. This response, however, does not distinguish between phorbol ester like and bryostatin-like behavior. In contrast, while many of the analogues contain a conserved C-ring in the binding domain and other features common to analogues with bryostatin-like properties, all analogues evaluated in the U937 proliferation and cell attachment assays displayed phorbol ester-like and/or toxic behavior, including WN-8, for which "bryostatin-like PKC modulatory activities" previously was suggested solely on the basis of PKC binding. These results underscore the importance of considering downstream biological effects, as tumor suppression cannot be inferred from potent PKC binding.
• Smith, Keith; Morris, Ian K.; Owen, Philip G., Journal of the Chemical Society. Perkin transactions I, 1988, p. 77 - 84
  作者：Smith, Keith、Morris, Ian K.、Owen, Philip G.、Bass, Robert J.

  DOI：——

  日期：——
• SMITH, KEITH;MORRIS, IAN K.;OWEN, PHILIP G.;BASS, ROBERT J., J. CHEM. SOC. PERKIN TRANS.,(1988) N 1, 77-83
  作者：SMITH, KEITH、MORRIS, IAN K.、OWEN, PHILIP G.、BASS, ROBERT J.

  DOI：——

  日期：——