甘氨酰二苯基硼酸 | 14335-29-6

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 甘氨酰二苯基硼酸
• 英文名称: 2,2-diphenyl-1,3,2-oxazaborolidine-5-one
• 英文别名: 2,2-diphenyl-1,3,2-oxazaborolidin-5-one；diphenyl 2-aminoethylborinate；Diphenylborinsaeure-aminoessigsaeure-anhydrid；Glycinatodiphenylboran；2-[(Diphenylboryl)oxy]-2-oxoethylamine；diphenylboranyl 2-aminoacetate
• CAS: 14335-29-6
• 化学式: C₁₄H₁₄BNO₂
• 分子量: 239.082
• InChiKey: IVHLNYVPKWICDY-UHFFFAOYSA-N

物化性质

• 沸点：
  353.5±44.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  DL-谷氨酰胺 、 甘氨酰二苯基硼酸 在 水 作用下， 以 乙醇 为溶剂， 反应 0.17h， 生成 Diphenylboranyl 2,5-diamino-5-oxopentanoate
  参考文献：
  名称：

  PROTEIN CROSS-LINKING INHIBITOR

  摘要：

  当前发明提供了一种含有由以下任一公式（1）-（13）表示的化合物的蛋白交联抑制剂，或其药用可接受的盐：R3—[—X—B(ZR1)—Y—B(ZR2)—W—]n—R4，  (1)R3—[—X—B(ZR1)—Y—]n—R4，  (2)R3—[—B(ZR1)—Y—B(ZR2)—W—]n—R4，  (3)R3—[—X—B(ZR1)—]n—R4，  (4)R3—[—B(ZR2)—W—]n—R4，  (5)R3—X—B(ZR1)-T[B(ZR2)—W—R4]2，  (6)R3—B(OH)2，  (7)R3—B(ZR1)—X—B(ZR2)—R4，  (8)R3—B(R1)—O—B(R2)—R4，  (9)R3—[—X—B(ZR1)—Y—B(ZR2)—]n—R4，  (10)R3—[—X—B(ZR1)—Y—B(ZR2)—W-Q-]n—R4，  (11)R3—[—P—X—B(ZR1)—Y—B(ZR2)—W—]n—R4，  (12)[R3—X—B(ZR1)—Y]2B(ZR2)，  (13)其中每个符号如说明书中所定义。

  公开号：

  US20110212919A1
• 作为产物：
  描述：

  二苯基酸 在 盐酸 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 4.0h， 生成 甘氨酰二苯基硼酸
  参考文献：
  名称：

  In vitro apoptotic activity of 2,2-diphenyl-1,3,2-oxazaborolidin-5-ones in L5178Y cells

  摘要：

  Compounds containing B-N bonds have shown interesting biological activity. One class of such molecules is the 2,2-diphenyl-1,3,2oxazaborolidin-5-ones (3a-j), which contain a B-N bond, have an alpha-amino acid moiety in the heterocycle, and have an exocyclic moiety related to an amino acid. The purpose of this work was to determine the inhibitory effects of 3a-j on the proliferation of murine L5178Y lymphoma cells. A new five-membered heterocyclic nucleus with apoptotic activity was found. The target products showed potent cytotoxicity in the L5178Y cell line. Among them, 3a exhibited the highest antineoplastic activity in L5178Y cells with an IC50 value of 22.5 +/- 0.2 mu M. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.lfs.2006.11.034

文献信息

• Preparation of Apoptotic Inducers, 2,2-Diphenyl-1,3,2-oxazaborolidin-5-ones, Under Alkaline Conditions
  作者：Benjamín Velasco-Bejarano、José Trujillo-Ferrara、René Miranda

  DOI：10.1055/s-2007-973886

  日期：2007.4

  An efficient and high-yielding procedure has been developed for the synthesis of a set of fifteen 2,2-diphenyl-1,3,2-oxazaborolidin-5-ones, through the reaction of the corresponding α-amino acid with diphenyl borinic acid under alkaline conditions (pH 7.5-8). It is of note that these compounds showed potent cytotoxic activity on K-562 and HCT-15 cell lines.

  一种高效且高产的合成方法已被开发出来，用于合成一组十五种2,2-二苯基-1,3,2-氧杂硼烷-5-酮，通过在碱性条件下（pH 7.5-8）将相应的α-氨基酸与二苯基硼酸反应。值得注意的是，这些化合物对K-562和HCT-15细胞系表现出强效的细胞毒活性。
• 2-Aminoethoxydiphenyl Borate as a Prototype Drug for a Group of Structurally Related Calcium Channel Blockers in Human Platelets
  作者：Yuliya Dobrydneva、Christopher J. Abelt、Beth Dovel、Celina M. Thadigiri、Roy L. Williams、Peter F. Blackmore

  DOI：10.1124/mol.105.015701

  日期：2006.1

  We have synthesized a series of 2-aminoethoxydiphenyl borate (2-APB, 2,2-diphenyl-1,3,2-oxazaborolidine) analogs and tested their ability to inhibit thrombin-induced Ca2+ influx in human platelets. The analogs were either synthesized by adding various substituents to the oxazaborolidine ring (methyl, dimethyl, tert -butyl, phenyl, methyl phenyl, and pyridyl) or increasing the size of the oxazaborolidine ring to seven- and nine-membered rings. NMR analysis of the boron-containing analogs suggests that each of them exist as a ring structure through the formation of an N→B coordinate bond (except for the hexyl analog). The possibility that these boron-containing compounds formed dimers was also considered. All compounds dose-dependently inhibited thrombin-induced Ca2+ influx in human platelets, with the 2,2-diphenyl-1,3,2-oxazaborolidine-5-one derivative having the weakest activity at 100 μM, whereas the ( S )-4-benzyl and ( R )-4-benzyl derivatives of 2-APB were approximately 10 times more potent than the parent 2-APB. Two nonboron analogs (3-methyl and 3- tert -butyl 2,2-diphenyl-1,3-oxazolidine) were synthesized; they had approximately the same activity as 2-APB, and this implies that the presence of boron was not necessary for inhibitory activity. All of the compounds tested were also able to inhibit thrombin-induced calcium release. We concluded that extensive modifications of the oxazaborolidine ring in 2-APB can be made, and Ca2+-blocking activity was maintained.

  我们合成了一系列 2-氨基乙氧基二苯基硼酸酯（2-APB，2,2-二苯基-1,3,2-噁唑硼烷）类似物，并测试了它们抑制凝血酶诱导的人体血小板 Ca2+ 流入的能力。这些类似物是通过在噁唑硼烷环上添加各种取代基（甲基、二甲基、叔丁基、苯基、甲基苯基和吡啶基）或将噁唑硼烷环的尺寸增加到七元环和九元环而合成的。对含硼类似物的核磁共振分析表明，它们中的每一种都是通过形成 N→B 坐标键而形成环状结构（己基类似物除外）。我们还考虑了这些含硼化合物形成二聚体的可能性。所有化合物都能剂量依赖性地抑制凝血酶诱导的人体血小板中 Ca2+ 的流入，其中 2,2-二苯基-1,3,2-噁唑硼烷-5-酮衍生物的活性最弱，为 100 μM，而 2-APB 的 ( S )-4- 苄基和 ( R )-4- 苄基衍生物的活性大约是母体 2-APB 的 10 倍。合成了两种非硼类似物（3-甲基和 3-叔丁基 2,2-二苯基-1,3-恶唑烷）；它们的活性与 2-APB 大致相同，这意味着硼的存在不是抑制活性的必要条件。所有测试化合物也都能抑制凝血酶诱导的钙释放。我们的结论是，可以对 2-APB 中的噁唑硼烷环进行广泛的修饰，并保持 Ca2+ 阻断活性。
• GALLOP, PAUL M.;HENSON, EDWARD;FLUCKIGER, RUDOLF
  作者：GALLOP, PAUL M.、HENSON, EDWARD、FLUCKIGER, RUDOLF

  DOI：——

  日期：——
• In vitro apoptotic activity of 2,2-diphenyl-1,3,2-oxazaborolidin-5-ones in L5178Y cells
  作者：Benjamín Velasco、José G. Trujillo-Ferrara、Luis H. Fabila Castillo、René Miranda、Luvia E. Sánchez-Torres

  DOI：10.1016/j.lfs.2006.11.034

  日期：2007.2

  Compounds containing B-N bonds have shown interesting biological activity. One class of such molecules is the 2,2-diphenyl-1,3,2oxazaborolidin-5-ones (3a-j), which contain a B-N bond, have an alpha-amino acid moiety in the heterocycle, and have an exocyclic moiety related to an amino acid. The purpose of this work was to determine the inhibitory effects of 3a-j on the proliferation of murine L5178Y lymphoma cells. A new five-membered heterocyclic nucleus with apoptotic activity was found. The target products showed potent cytotoxicity in the L5178Y cell line. Among them, 3a exhibited the highest antineoplastic activity in L5178Y cells with an IC50 value of 22.5 +/- 0.2 mu M. (c) 2006 Elsevier Inc. All rights reserved.
• PROTEIN CROSS-LINKING INHIBITOR
  申请人：Mikoshiba Katsuhiko

  公开号：US20110212919A1

  公开（公告）日：2011-09-01

  The present invention provides a protein cross-linking inhibitor containing a compound represented by any of the following formulas ( 1 )-( 13 ), or a pharmaceutically acceptable salt thereof: R 3 —[—X—B(ZR 1 )—Y—B(ZR 2 )—W—] n —R 4 ,  (1) R 3 —[—X—B(ZR 1 )—Y—] n —R 4 ,  (2) R 3 —[—B(ZR 1 )—Y—B(ZR 2 )—W—] n —R 4 ,  (3) R 3 —[—X—B(ZR 1 )—] n —R 4 ,  (4) R 3 —[—B(ZR 2 )—W—] n —R 4 ,  (5) R 3 —X—B(ZR 1 )-T[B(ZR 2 )—W—R 4 ] 2 ,  (6) R 3 —B(OH) 2 ,  (7) R 3 —B(ZR 1 )—X—B(ZR 2 )—R 4 ,  (8) R 3 —B(R 1 )—O—B(R 2 )—R 4 ,  (9) R 3 —[—X—B(ZR 1 )—Y—B(ZR 2 )—] n —R 4 ,  (10) R 3 —[—X—B(ZR 1 )—Y—B(ZR 2 )—W-Q-] n —R 4 ,  (11) R 3 —[—P—X—B(ZR 1 )—Y—B(ZR 2 )—W—] n —R 4 ,  (12) [R 3 —X—B(ZR 1 )—Y] 2 B(ZR 2 ),  (13) wherein each symbol is as defined in the DESCRIPTION.

  当前发明提供了一种含有由以下任一公式（1）-（13）表示的化合物的蛋白交联抑制剂，或其药用可接受的盐：R3—[—X—B(ZR1)—Y—B(ZR2)—W—]n—R4，  (1)R3—[—X—B(ZR1)—Y—]n—R4，  (2)R3—[—B(ZR1)—Y—B(ZR2)—W—]n—R4，  (3)R3—[—X—B(ZR1)—]n—R4，  (4)R3—[—B(ZR2)—W—]n—R4，  (5)R3—X—B(ZR1)-T[B(ZR2)—W—R4]2，  (6)R3—B(OH)2，  (7)R3—B(ZR1)—X—B(ZR2)—R4，  (8)R3—B(R1)—O—B(R2)—R4，  (9)R3—[—X—B(ZR1)—Y—B(ZR2)—]n—R4，  (10)R3—[—X—B(ZR1)—Y—B(ZR2)—W-Q-]n—R4，  (11)R3—[—P—X—B(ZR1)—Y—B(ZR2)—W—]n—R4，  (12)[R3—X—B(ZR1)—Y]2B(ZR2)，  (13)其中每个符号如说明书中所定义。