8-amino-7-oxo-octanoic acid hydrochloride | 168689-41-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-amino-7-oxo-octanoic acid hydrochloride
• 英文别名: Octanoic acid, 8-amino-7-oxo-, hydrochloride (1:1)；8-amino-7-oxooctanoic acid;hydrochloride
• CAS: 168689-41-6
• 化学式: C₈H₁₅NO₃*ClH
• 分子量: 209.673
• InChiKey: UUDMHRYCKXFSKE-UHFFFAOYSA-N

物化性质

• 熔点：
  129-131 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-amino-7-oxo-octanoic acid hydrochloride 在 platinum(IV) oxide 吡啶 、 盐酸 、 sodium hydroxide 、 盐酸羟胺 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 20.0~40.0 ℃ 、448.17 kPa 条件下， 反应 120.0h， 生成 6-(2-oxo-imidazolidin-4-yl)-hexanoic acid
  参考文献：
  名称：

  Inhibitors of biotin biosynthesis as potential herbicides

  摘要：

  Isosteric derivatives and analogues of the 7-keto-8-aminopelargonic acid (KAPA), 7,8-diaminopelargonic acid (DAPA) and desthiobiotin (DTB) vitamer intermediates involved in the biosynthetic pathway of biotin were prepared and evaluated as potential herbicides. The most active compound was desmethyl-KAPA which displayed a GR(50) (concentration of the active compound that causes a 50% growth inhibition) value of 8 ppm, where values <50 ppm are considered herbicidal. Other KAPA analogs where the terminal Me group was replaced by bulkier substituents such as Et, i-Pr and HOCH2 showed moderate activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.047
• 作为产物：
  描述：

  乙基5-碘戊酸酯 在 盐酸 、 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 生成 8-amino-7-oxo-octanoic acid hydrochloride
  参考文献：
  名称：

  Inhibitors of biotin biosynthesis as potential herbicides

  摘要：

  Isosteric derivatives and analogues of the 7-keto-8-aminopelargonic acid (KAPA), 7,8-diaminopelargonic acid (DAPA) and desthiobiotin (DTB) vitamer intermediates involved in the biosynthetic pathway of biotin were prepared and evaluated as potential herbicides. The most active compound was desmethyl-KAPA which displayed a GR(50) (concentration of the active compound that causes a 50% growth inhibition) value of 8 ppm, where values <50 ppm are considered herbicidal. Other KAPA analogs where the terminal Me group was replaced by bulkier substituents such as Et, i-Pr and HOCH2 showed moderate activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.047

文献信息

• The design and synthesis of inhibitors of dethiobiotin synthetase as potential herbicides
  作者：Alan R Rendina、Wendy S Taylor、Katharine Gibson、George Lorimer、Dennis Rayner、Bruce Lockett、Kevin Kranis、Barry Wexler、Dana Marcovici-Mizrahi、Ayelet Nudelman、Abraham Nudelman、Eileen Marsilii、Hongji Chi、Zdislaw Wawrzak、Joseph Calabrese、Weijun Huang、Jia Jia、Gunter Schneider、Ylva Lindqvist、Guang Yang

  DOI：10.1002/(sici)1096-9063(199903)55:3<236::aid-ps888>3.0.co;2-0

  日期：1999.3

  Dethiobiotin synthetase (DTBS;E.C. 6.6.6.6), the penultimate enzyme in the biosynthesis of the essential vitamin biotin, is a new potential target for novel herbicides. Inhibitors were designed based on mechanistic and structural information. The in-vitro activities of these potential inhibitors versus the bacterial enzyme are reported here. Mimics of 7,8-diaminopelargonic acid (DAPA) or the DAPA carbamate reaction intermediate were substrates or partial substrates for the enzyme. Synergistic binding with ATP was noted with compounds which contained an amino functionality, NMR studies and X-ray structures confirmed that the inhibitors could be phosphorylated by the enzyme. Several series of potential inhibitors were designed to take advantage of this partial substrate activity by generating potentially more tightly bound phosphorylated inhibitors in situ, Structure-activity relationships for these series based on both substrate and inhibitory activity are described herein. An X-ray structure for one of these inhibitors is also discussed. Although considerable potential for inhibitors of this type was demonstrated, none of the compounds reported showed sufficient herbicidal activity to be a commercial proposition. (C) 1999 Society of Chemical Industry.
• Inhibitors of biotin biosynthesis as potential herbicides
  作者：Ayelet Nudelman、Dana Marcovici-Mizrahi、Abraham Nudelman、Dennis Flint、Vernon Wittenbach

  DOI：10.1016/j.tet.2003.12.047

  日期：2004.2

  Isosteric derivatives and analogues of the 7-keto-8-aminopelargonic acid (KAPA), 7,8-diaminopelargonic acid (DAPA) and desthiobiotin (DTB) vitamer intermediates involved in the biosynthetic pathway of biotin were prepared and evaluated as potential herbicides. The most active compound was desmethyl-KAPA which displayed a GR(50) (concentration of the active compound that causes a 50% growth inhibition) value of 8 ppm, where values <50 ppm are considered herbicidal. Other KAPA analogs where the terminal Me group was replaced by bulkier substituents such as Et, i-Pr and HOCH2 showed moderate activity. (C) 2003 Elsevier Ltd. All rights reserved.