((octanedioylbis(azanediyl))bis(3,1-phenylene))diboronic acid

• 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: ((octanedioylbis(azanediyl))bis(3,1-phenylene))diboronic acid
• 英文别名: [3-[[8-(3-Boronoanilino)-8-oxooctanoyl]amino]phenyl]boronic acid；[3-[[8-(3-boronoanilino)-8-oxooctanoyl]amino]phenyl]boronic acid
• 化学式: C₂₀H₂₆B₂N₂O₆
• 分子量: 412.058
• InChiKey: AGTURTVACVFYDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.04
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  139
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N¹,N⁸-bis(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)octanediamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以67%的产率得到((octanedioylbis(azanediyl))bis(3,1-phenylene))diboronic acid
  参考文献：
  名称：

  新型二价连接模式苯硼酸衍生物的制备及其生物学评价

  摘要：

  We report a new route to the preparation of C-2-symmetrical bivalent phenylboronic acids having alkyl linker groups in the molecule and results of biological evaluation of their biological activity and cytotoxic activity against Vero cells. Among the tested compounds, C-2-symmetrical bivalent meta-oriented phenylboronic acid 2f (n=7) showed high cytotoxic activity (CC50=5.43 mu M) against Vero cells. The results of an SAR study suggested that the presence of a C7-methylene linker group in the molecule is an important structural factor for expression of potential cytotoxic activities. A sugar recognition property of this C-2-symmetrical geometric molecule was suggested by NMR analysis of compound 2f with methyl alpha-D-glucopyranoside 6.

  DOI：

  10.3987/com-18-13899

文献信息

• Preparation and Biological Activity of Novel Twin-Drug Type C2-Symmetrical Cyclic Phenylboronic Acid Derivatives
  作者：Kunihiro Sumoto、Makoto Furutachi、Ayumi Ejima、Reika Tsuru、Saho Goto、Toshiaki Gondo、Kenta Ako、Saho Fuchigami、Saya Fujii、Arisa Okumura、Ayumi Tozuka、Kazumi Yokomizo、Jian-Rong Zhou、Hiroshi Inao、Yutaro Ono、Nobuhiro Kashige、Fumio Miake

  DOI：10.3987/com-16-s(s)9

  日期：——

  We here report the results of evaluation of antibacterial and anti-herpes simplex virus-1 (HSV-1) activities of a novel twin-drug type C-2-symmetrical boronic acid and its pinacol ester derivatives. By using a primitive amide bond formation reaction, various targeted C-2-symmetrical cyclic phenylboronic acid derivatives were obtained from the reactions of commercially available amino-substituted phenylboronic acid derivatives and diacid dichlorides. The C-2-symmetrical bivalent molecule 3bd containing two cyclic phenylboronic acid pinacol ester moieties and a flexible hexamethylene linker showed both antibacterial activity (S. aureus) and anti-HSV-1 activity. The corresponding boronic acid derivative 3dd showed neither antibacterial nor anti-HSV-1 activity, indicating the importance of two pinacol ester functionalities.
• Preparation of Novel Bivalent Linker Mode Phenylboronic Acid Derivatives and Their Biological Evaluation
  作者：Kunihiro Sumoto、Makoto Furutachi、Ayaka Matsumoto、Tetsuya Tamenaga、Aya Sugita、Misato Kuroiwa、Kazumi Yokomizo、Jian-Rong Zhou、Nobuhiro Kashige、Fumio Miake

  DOI：10.3987/com-18-13899

  日期：——

  We report a new route to the preparation of C-2-symmetrical bivalent phenylboronic acids having alkyl linker groups in the molecule and results of biological evaluation of their biological activity and cytotoxic activity against Vero cells. Among the tested compounds, C-2-symmetrical bivalent meta-oriented phenylboronic acid 2f (n=7) showed high cytotoxic activity (CC50=5.43 mu M) against Vero cells. The results of an SAR study suggested that the presence of a C7-methylene linker group in the molecule is an important structural factor for expression of potential cytotoxic activities. A sugar recognition property of this C-2-symmetrical geometric molecule was suggested by NMR analysis of compound 2f with methyl alpha-D-glucopyranoside 6.