1-(7-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-(2-(2-hydroxypropan-2-yl)pyrimidin-5-yl)benzo[d]thiazol-2-yl)-3-ethyl-5-methyl-1,3,5-triazinan-2-one | 1459772-72-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(7-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-(2-(2-hydroxypropan-2-yl)pyrimidin-5-yl)benzo[d]thiazol-2-yl)-3-ethyl-5-methyl-1,3,5-triazinan-2-one
• 英文别名: 1-(7-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-5-(2-(2-hydroxypropan-2-yl)pyrimidin-5-yl)benzo[d]thiazol-2-yl)-3-ethyl-5-methyl-1,3,5-triazinan-2-one；1-[7-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-[2-(2-hydroxypropan-2-yl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-5-methyl-1,3,5-triazinan-2-one
• CAS: 1459772-72-5
• 化学式: C₂₅H₃₃BN₆O₄S
• 分子量: 524.452
• InChiKey: LSOKNODKQSKDJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(7-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-(2-(2-hydroxypropan-2-yl)pyrimidin-5-yl)benzo[d]thiazol-2-yl)-3-ethyl-5-methyl-1,3,5-triazinan-2-one 在 盐酸 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 1-[7-[4-[(cyclopropylamino)methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea
  参考文献：
  名称：

  Discovery and in vivo evaluation of alcohol-containing benzothiazoles as potent dual-targeting bacterial DNA supercoiling inhibitors

  摘要：

  A series of dual-targeting, alcohol-containing benzothiazoles has been identified with superior antibacterial activity and drug-like properties. Early lead benzothiazoles containing carboxylic acid moieties showed efficacy in a well-established in vivo model, but inferior drug-like properties demanded modifications of functionality capable of demonstrating superior efficacy. Eliminating the acid group in favor of hydrophilic alcohol moieties at C(5), as well as incorporating solubilizing groups at the C(7) position of the core ring provided potent, broad-spectrum Gram-positive antibacterial activity, lower protein binding, and markedly improved efficacy in vivo.

  DOI：

  10.1016/j.bmcl.2014.07.037
• 作为产物：
  描述：

  5-溴-2-嘧啶甲酸甲酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四(三苯基膦)钯 、 potassium acetate 、 三环己基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 6.5h， 生成 1-(7-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-(2-(2-hydroxypropan-2-yl)pyrimidin-5-yl)benzo[d]thiazol-2-yl)-3-ethyl-5-methyl-1,3,5-triazinan-2-one
  参考文献：
  名称：

  Antibacterial Compounds

  摘要：

  本发明提供了以下式的化合物，其盐、拉克酸盐、对映体、对映异构体、酯、氨基甲酸酯、磷酸酯、硫酸酯、氘代形式及其前药。 还提供了将这些化合物用作抗菌剂、包含它们的组合物以及它们的制造方法。

  公开号：

  US20130252938A1

文献信息

• ANTIBACTERIAL COMPUNDS
  申请人：Biota Europe Ltd

  公开号：US20150329530A1

  公开（公告）日：2015-11-19

  The present invention provides a compound of the following formula, salts, racemates, diastereomers, enantiomers, esters, carbamates, phosphates, sulfates, deuterated forms and prodrugs thereof. Also provided is the use of these compounds as antibacterials, compositions comprising them and processes for their manufacture.

  本发明提供以下式子的化合物，其盐，外消旋体，对映体，酯，氨基甲酸酯，磷酸酯，硫酸酯，氘代形式和前药。此外，还提供这些化合物作为抗菌剂的用途，包含它们的组合物以及它们的制造过程。
• Antibacterial Compounds
  申请人：BIOTA EUROPE LTD.

  公开号：US20130252938A1

  公开（公告）日：2013-09-26

  The present invention provides a compound of the following formula, salts, racemates, diastereomers, enantiomers, esters, carbamates, phosphates, sulfates, deuterated forms and prodrugs thereof. Also provided is the use of these compounds as antibacterials, compositions comprising them and processes for their manufacture.

  本发明提供了以下式的化合物，其盐、拉克酸盐、对映体、对映异构体、酯、氨基甲酸酯、磷酸酯、硫酸酯、氘代形式及其前药。 还提供了将这些化合物用作抗菌剂、包含它们的组合物以及它们的制造方法。
• Discovery and in vivo evaluation of alcohol-containing benzothiazoles as potent dual-targeting bacterial DNA supercoiling inhibitors
  作者：James T. Palmer、Lorraine C. Axford、Stephanie Barker、James M. Bennett、Michael Blair、Ian Collins、David T. Davies、Leigh Ford、Carlie T. Gannon、Paul Lancett、Alastair Logan、Christopher J. Lunniss、Craig J. Morton、Daniel A. Offermann、Gary R.W. Pitt、B. Narasinga Rao、Amit K. Singh、Tarun Shukla、Anil Srivastava、Neil R. Stokes、Helena B. Thomaides-Brears、Anju Yadav、David J. Haydon

  DOI：10.1016/j.bmcl.2014.07.037

  日期：2014.9

  A series of dual-targeting, alcohol-containing benzothiazoles has been identified with superior antibacterial activity and drug-like properties. Early lead benzothiazoles containing carboxylic acid moieties showed efficacy in a well-established in vivo model, but inferior drug-like properties demanded modifications of functionality capable of demonstrating superior efficacy. Eliminating the acid group in favor of hydrophilic alcohol moieties at C(5), as well as incorporating solubilizing groups at the C(7) position of the core ring provided potent, broad-spectrum Gram-positive antibacterial activity, lower protein binding, and markedly improved efficacy in vivo.