5-(hydroxymethyl)benzo[c][1,2]oxaborol-1(3H)-ol | 905710-77-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 5-(hydroxymethyl)benzo[c][1,2]oxaborol-1(3H)-ol
• 英文别名: (1-hydroxy-3H-2,1-benzoxaborol-5-yl)methanol；5-(hydroxymethyl)-3H-2,1-benzoxaborol-1-ol；1,3-dihydro-1-hydroxy-5-hydroxymethyl-2,1-benzoxaborole
• CAS: 905710-77-2
• 化学式: C₈H₉BO₃
• 分子量: 163.969
• InChiKey: ZBVCPDWREFJZOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(hydroxymethyl)benzo[c][1,2]oxaborol-1(3H)-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到1-羟基-1,3-二氢苯并[C][1,2]氧杂硼烷基-5-甲醛
  参考文献：
  名称：

  INHIBITORS OF THE YAP/TAZ-TEAD INTERACTION AND THEIR USE IN THE TREATMENT OF CANCER

  摘要：

  该发明涉及以下化合物的公式(I)：其中R1; R2, R3, R4, R5和如描述中定义的。公式(I)的化合物是YAP/TAZ-TEAD相互作用的抑制剂，因此在癌症治疗中有用。

  公开号：

  EP3632908A1
• 作为产物：
  描述：

  4-溴-1,3-苯二甲酸 在 盐酸 、 正丁基锂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 5-(hydroxymethyl)benzo[c][1,2]oxaborol-1(3H)-ol
  参考文献：
  名称：

  Discovery of a New Boron-Containing Antifungal Agent, 5-Fluoro-1,3-dihydro-1-hydroxy-2,1- benzoxaborole (AN2690), for the Potential Treatment of Onychomycosis

  摘要：

  A structure-activity relationship investigation for a more efficacious therapy to treat onychomycosis, a fungal infection of the toe and fingernails, led to the discovery of a boron-containing small molecule, 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (AN2690), which is currently in clinical trials for onychomycosis topical treatment.

  DOI：

  10.1021/jm0603724

文献信息

• Synthesis of Amino- and Hydroxymethyl Benzoxaboroles: Prominent Scaffolds for Further Functionalization
  作者：Rodrigo S. Fuscaldo、Pedro H. V. Vontobel、Eduam O. Boeira、Angélica V. Moro、Jessie S. da Costa

  DOI：10.1002/ejoc.201900013

  日期：2019.3.14

  The development of a short, simple, and efficient synthesis of amino‐ and hydroxymethyl‐substituted benzoxaboroles is described. The key step was the early stage incorporation of the boron by the borylation of an aniline. The formed boronates were then elaborated to the final products in two additional steps, in good yields.

  本文描述了一种短，简单而有效的合成氨基和羟甲基取代的苯并氧杂硼酸的方法的开发。关键步骤是通过苯胺的硼化使硼早期掺入。然后将形成的硼酸盐分两步精加工成最终产品，收率很高。
• Hydrolytically-Resistant Boron-Containing Therapeutics And Methods Of Use
  申请人：Lee Ving

  公开号：US20070265226A1

  公开（公告）日：2007-11-15

  Compositions and methods of use of boron derivatives, including benzoxaboroles, benzazaboroles and benzthiaboroles, as therapeutic agents for treatment of diseases caused by fungi, yeast, bacteria or viruses are disclosed, as well as methods for synthesis of said agents and compositions thereof.

  本发明公开了硼衍生物的组合物和使用方法，包括苯并噻硼酸酯、苯并氮硼酸酯和苯并硫硼酸酯，作为治疗真菌、酵母、细菌或病毒引起的疾病的治疗剂，以及合成该剂和其组合物的方法。
• Compounds for the Treatment of Periodontal Disease
  申请人：Sanders Virginia

  公开号：US20070286822A1

  公开（公告）日：2007-12-13

  Compounds, compositions and methods are provided which are useful in the treatment of periodontal disease.

  本发明提供了一种在治疗牙周疾病方面有用的化合物、组合物和方法。
• Hydrolytically-resistant boron-containing therapeutics and methods of use
  申请人：Anacor Pharmaceuticals, Inc.

  公开号：US08106031B2

  公开（公告）日：2012-01-31

  Compositions and methods of use of boron derivatives, including benzoxaboroles, benzazaboroles and benzthiaboroles, as therapeutic agents for treatment of diseases caused by fungi, yeast, bacteria or viruses are disclosed, as well as methods for synthesis of said agents and compositions thereof.

  本文披露了硼衍生物的组成和使用方法，包括苯并氧硼烷、苯并氮硼烷和苯并硫硼烷，作为治疗由真菌、酵母、细菌或病毒引起的疾病的治疗剂，以及制备这些治疗剂和组合物的方法。
• Discovery of a New Boron-Containing Antifungal Agent, 5-Fluoro-1,3-dihydro-1-hydroxy-2,1- benzoxaborole (AN2690), for the Potential Treatment of Onychomycosis
  作者：Stephen J. Baker、Yong-Kang Zhang、Tsutomu Akama、Agnes Lau、Huchen Zhou、Vincent Hernandez、Weimin Mao、M. R. K. Alley、Virginia Sanders、Jacob J. Plattner

  DOI：10.1021/jm0603724

  日期：2006.7.1

  A structure-activity relationship investigation for a more efficacious therapy to treat onychomycosis, a fungal infection of the toe and fingernails, led to the discovery of a boron-containing small molecule, 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (AN2690), which is currently in clinical trials for onychomycosis topical treatment.