7-aminomethyl-1,3-dihydro-1-hydroxy-2,1-benzoxaborole | 1268335-91-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 7-aminomethyl-1,3-dihydro-1-hydroxy-2,1-benzoxaborole
• 英文别名: 7-(Aminomethyl)benzo[c][1,2]oxaborol-1(3H)-ol；(1-hydroxy-3H-2,1-benzoxaborol-7-yl)methanamine
• CAS: 1268335-91-6
• 化学式: C₈H₁₀BNO₂
• 分子量: 162.984
• InChiKey: WFCXNRARUJVXLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 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：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-aminomethyl-1,3-dihydro-1-hydroxy-2,1-benzoxaborole 、 9-(O-carboxymethyloxime)clarithromycin 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以32%的产率得到[7-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole)methyl]amide 9-clarithromycinmethoxyoxime
  参考文献：
  名称：

  Two approaches to the use of benzo[c][1,2]oxaboroles as active fragments for synthetic transformation of clarithromycin

  摘要：

  Clarithromycin (active against Gram positive infections) and 1-hydroxy-1,3-dihydrobenzo[c][1,2] oxaborole derivatives (effective for Gram negative microbes) are the ligands of bacterial RNA. The antimicrobial activities of these benzoxaboroles linked with clarithromycin at 9 or 400 position were compared. Two synthetic pathways for these conjugates were elaborated. First pathway explored the substitution of the C-9 carbonyl group of macrolactone's cycle via oxime linker, the second direction used the modification of the 400-O-group of cladinose via the formation of carbamates of benzoxaboroles. 4''-O-(3-S-(1-Hydroxy-1,3-dihydro-benzo[c][1,2] oxaborole)-methyl-carbamoyl-clarithromycin showed twofold decrease in MICs for S. epidermidis and S. pneumoniae than clarithromycin. 4''-O-Modified clarithromycin demonstrated an efficacy against Gram positive strains only. Compounds with C-9 substitution were more active than 4''-O-substituted antibiotics for susceptible strains E. coli tolC and did not exceed the activity of initial antibiotics.

  DOI：

  10.1080/14756366.2016.1261129
• 作为产物：
  描述：

  2,6-二甲基溴苯 在 sodium tetrahydroborate 、 potassium permanganate 、 lithium aluminium tetrahydride 、 锂硼氢 、 正丁基锂 、 氯化亚砜 、 氨 、 水 、 silica gel 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 、 叔丁醇 为溶剂， 反应 35.41h， 生成 7-aminomethyl-1,3-dihydro-1-hydroxy-2,1-benzoxaborole
  参考文献：
  名称：

  [EN] BORON-CONTAINING SMALL MOLECULES AS ANTIPROTOZOAL AGENTS
  [FR] PETITES MOLÉCULES CONTENANT DU BORE EN TANT QU'AGENTS ANTI-PROTOZOAIRES

  摘要：

  这项发明提供了以下公式的新化合物，用于治疗原虫感染，包含这些化合物的药物组合物，以及这些化合物与至少一种额外治疗有效药剂的组合。

  公开号：

  WO2011022337A1

文献信息

• BORON-CONTAINING SMALL MOLECULES AS ANTIPROTOZOAL AGENTS
  申请人：Zhou Huchen

  公开号：US20110207701A1

  公开（公告）日：2011-08-25

  This invention provides, among other things, novel compounds useful for treating protozoal infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective agent.

  该发明提供了用于治疗原虫感染的新化合物，含有这些化合物的制药组合物，以及这些化合物与至少一种额外的治疗有效剂的组合。
• [EN] BORON-CONTAINING SMALL MOLECULES AS ANTIPROTOZOAL AGENTS<br/>[FR] PETITES MOLÉCULES CONTENANT DU BORE EN TANT QU'AGENTS ANTI-PROTOZOAIRES
  申请人：ANACOR PHARMACEUTICALS INC

  公开号：WO2011022337A1

  公开（公告）日：2011-02-24

  This invention provides novel compounds of the following formula useful for treating protozoal infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective agent.

  这项发明提供了以下公式的新化合物，用于治疗原虫感染，包含这些化合物的药物组合物，以及这些化合物与至少一种额外治疗有效药剂的组合。
• Two approaches to the use of benzo[c][1,2]oxaboroles as active fragments for synthetic transformation of clarithromycin
  作者：Gennady B. Lapa、Elena P. Mirchink、Elena B Isakova、Maria N Preobrazhenskaya

  DOI：10.1080/14756366.2016.1261129

  日期：2017.1.1

  Clarithromycin (active against Gram positive infections) and 1-hydroxy-1,3-dihydrobenzo[c][1,2] oxaborole derivatives (effective for Gram negative microbes) are the ligands of bacterial RNA. The antimicrobial activities of these benzoxaboroles linked with clarithromycin at 9 or 400 position were compared. Two synthetic pathways for these conjugates were elaborated. First pathway explored the substitution of the C-9 carbonyl group of macrolactone's cycle via oxime linker, the second direction used the modification of the 400-O-group of cladinose via the formation of carbamates of benzoxaboroles. 4''-O-(3-S-(1-Hydroxy-1,3-dihydro-benzo[c][1,2] oxaborole)-methyl-carbamoyl-clarithromycin showed twofold decrease in MICs for S. epidermidis and S. pneumoniae than clarithromycin. 4''-O-Modified clarithromycin demonstrated an efficacy against Gram positive strains only. Compounds with C-9 substitution were more active than 4''-O-substituted antibiotics for susceptible strains E. coli tolC and did not exceed the activity of initial antibiotics.