N-((羟基氨基甲酰)甲基)苯甲酰胺 | 1499-54-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-((羟基氨基甲酰)甲基)苯甲酰胺
• 英文名称: Hippuryl-hydroxamsaeure
• 英文别名: N-(2-(hydroxyamino)-2-oxoethyl)benzamide；Hippurohydroxamic acid；N-[2-(hydroxyamino)-2-oxoethyl]benzamide
• CAS: 1499-54-3
• 化学式: C₉H₁₀N₂O₃
• mdl: MFCD01672906
• 分子量: 194.19
• InChiKey: WYFKHRKLNSAEBW-UHFFFAOYSA-N

物化性质

• 熔点：
  158.5 °C
• 沸点：
  330.62°C (rough estimate)
• 密度：
  1.2934 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

制备方法与用途

类别：有毒物品

可燃性危险特性

• 可燃；燃烧时产生有毒氮氧化物烟雾

储运特性

• 通风、低温、干燥

灭火剂

• 干粉、泡沫、沙土、二氧化碳、雾状水

反应信息

• 作为反应物：
  描述：

  N-((羟基氨基甲酰)甲基)苯甲酰胺 在 氢氧化钾 、 羟胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 生成 N-Benzoyl-glycyl-glycyl-hydroxamsaeure
  参考文献：
  名称：

  A Peptide Synthesis via Hydroxamic Acids

  摘要：

  DOI：

  10.1021/jo01026a501
• 作为产物：
  描述：

  马尿酸乙酯 在 氢氧化钾 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 生成 N-((羟基氨基甲酰)甲基)苯甲酰胺
  参考文献：
  名称：

  Therapy for urolithiasis with hydroxamic acids. I. Synthesis of new N-(aroyl)glycinohydroxamic acid derivatives and related compounds.

  摘要：

  为了寻找针对尿路结石的治疗药物，我们合成了四十三种新的N-(芳酰基)-甘氨酸羟肟酸衍生物及相关化合物，并检测了它们的脲酶抑制活性。同时，我们还确定了这些化合物在大鼠体内的尿液排泄情况。

  DOI：

  10.1248/cpb.28.2045

文献信息

• Controlling Plasma Stability of Hydroxamic Acids: A MedChem Toolbox
  作者：Paul Hermant、Damien Bosc、Catherine Piveteau、Ronan Gealageas、BaoVy Lam、Cyril Ronco、Matthieu Roignant、Hasina Tolojanahary、Ludovic Jean、Pierre-Yves Renard、Mohamed Lemdani、Marilyne Bourotte、Adrien Herledan、Corentin Bedart、Alexandre Biela、Florence Leroux、Benoit Deprez、Rebecca Deprez-Poulain

  DOI：10.1021/acs.jmedchem.7b01444

  日期：2017.11.9

  Hydroxamic acids are outstanding zinc chelating groups that can be used to design potent and selective metalloenzyme inhibitors in various therapeutic areas. Some hydroxamic acids display a high plasma clearance resulting in poor in vivo activity, though they may be very potent compounds in vitro. We designed a 57-member library of hydroxamic acids to explore the structure–plasma stability relationships

  异羟肟酸是杰出的锌螯合基团，可用于设计各种治疗领域中的有效和选择性金属酶抑制剂。一些异羟肟酸显示出较高的血浆清除率，导致体内活性差，尽管它们在体外可能是非常有效的化合物。我们设计了一个由57名成员组成的异羟肟酸文库，以探索这些系列中结构与血浆的稳定性关系，并确定哪些酶和哪些药效团对血浆稳定性至关重要。芳基酯酶和羧酸酯酶被确定为异羟肟酸的主要代谢酶。最后，我们建议引入或删除结构特征以提高稳定性。因此，这项工作提供了第一个药物化学工具箱（实验程序和结构指导），用于评估和控制异羟肟酸的血浆稳定性，并充分发挥其作为体内药理探针和治疗剂的潜力。这项研究与临床前开发特别相关，因为它允许获得在人和啮齿动物模型中同样稳定的化合物。
• Therapy for urolithiasis with hydroxamic acids. I. Synthesis of new N-(aroyl)glycinohydroxamic acid derivatives and related compounds.
  作者：KEIICHI MUNAKATA、SATORU TANAKA、SHOJI TOYOSHIMA

  DOI：10.1248/cpb.28.2045

  日期：——

  With the aim of finding a therapeutic agent for urolithiasis, forty-three new N-(aroyl)-glycinohydroxamic acid derivatives and related compounds were synthesized and examined for urease inhibitory activity. Their urinary excretion in rats was also determined.

  为了寻找针对尿路结石的治疗药物，我们合成了四十三种新的N-(芳酰基)-甘氨酸羟肟酸衍生物及相关化合物，并检测了它们的脲酶抑制活性。同时，我们还确定了这些化合物在大鼠体内的尿液排泄情况。
• Botvinik,M.M. et al., Journal of general chemistry of the USSR, 1962, vol. 32, p. 1369 - 1375
  作者：Botvinik,M.M. et al.

  DOI：——

  日期：——
• The Reaction of Formohydroxamic Acid with Acyl Derivatives in Neutral Aqueous Solution
  作者：Sidney A. Bernhard、Yeichiel. Shalitin、Zohrab H. Tashjian

  DOI：10.1021/ja01074a036

  日期：1964.10
• Effect of acute elevation of IGF-I on circulating GH, TSH, insulin, IGF-II and IGFBP-3 levels in non-endocrine short stature (NESS)
  作者：Kunihiko Hanew、A. Tanaka

  DOI：10.1007/bf03343801

  日期：2001.1

  It is not clear whether acute and slight elevation of serum IGF-I, which does not affect blood glucose levels, modulates circulating GH levels. To clarify this, small doses of recombinant human IGF-I (rhIGF-I, 5 microg/kg, i.v.) were administered as a bolus to 10 children with non-endocrine short stature (NESS) (5 males and 5 females, 11.2+/-0.7 yr old) after an overnight fast. Physiological saline was administered intravenously to sex- and age-matched NESS controls (5 males and 5 females, 10.9+/-0.7 yr old). The changes of serum GH, TSH, PRL, IGF-I, IGF-II, IGFBP-3, T4, T3 and plasma glucose levels after the administration were compared to those of the control subjects. Serum IGF-I levels increased significantly from 15 to 150 min after injection compared to those in the control group. The peak value was observed at 15 min (delta increment, 74.6+/-11.8 microg/l). At 15 min after the injection, serum insulin was suppressed significantly (p<0.05), although plasma glucose levels were not modified significantly. Serum TSH showed a significant decrease by rhIGF-I at 15 min and 60 min, whereas serum T4 and T3 levels were not modified. Serum GH was also significantly suppressed at 60 min (p<0.02) and showed a rebound increase at 120 min (p<0.05). Serum IGFBP-3 levels after rhIGF-I were higher than controls at 90 min and 150 min. No significant changes of serum PRL, IGF-II, (IGF-I plus IGF-II)/IGFBP-3 ratios were observed after the IGF-I injection compared to controls. These results indicate that circulating IGF-I is a physiological regulator of GH secretion in normal children, since the changes of IGF-I after the small doses of rhlGF-I administration were within physiological ranges and did not affect plasma glucose levels.