3,4-dimethoxycinnamohydroxamic acid | 25356-83-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3,4-dimethoxycinnamohydroxamic acid
• 英文别名: 3,4-dimethoxyphenylpropenoyl hydroxamic acid；3-(3,4-Dimethoxyphenyl)-2-propenehydroximic acid；3-(3,4-dimethoxyphenyl)-N-hydroxyprop-2-enamide
• CAS: 25356-83-6
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: FAKIVHFFVVPOKL-UHFFFAOYSA-N

物化性质

• 熔点：
  187-190 °C(Solv: ethanol (64-17-5))
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxycinnamohydroxamic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以94%的产率得到3-(3,4-dimethoxyphenyl)propiohydroxamic acid
  参考文献：
  名称：

  Chemical intervention in bacterial lignin degradation pathways: Development of selective inhibitors for intradiol and extradiol catechol dioxygenases

  摘要：

  Bacterial lignin degradation could be used to generate aromatic chemicals from the renewable resource lignin, provided that the breakdown pathways can be manipulated. In this study, selective inhibitors of enzymatic steps in bacterial degradation pathways were developed and tested for their effects upon lignin degradation. Screening of a collection of hydroxamic acid metallo-oxygenase inhibitors against two catechol dioxygenase enzymes, protocatechuate 3,4-dioxygenase (3,4-PCD) and 2,3-dihydroxyphenylpropionate 1,2-dioxygenase (MhpB), resulted in the identification of selective inhibitors D13 for 3,4-PCD (IC50 15 mu M) and D3 for MhpB (IC50 110 mu M). Application of D13 to Rhodococcus jostii RHA1 in minimal media containing ferulic acid led to the appearance of metabolic precursor protocatechuic acid at low concentration. Application of 1 mM disulfiram, an inhibitor of mammalian aldehyde dehydrogenase, to R. jostii RHA1, gave rise to 4-carboxymuconolactone on the beta-ketoadipate pathway, whereas in Pseudomonas fluorescens Pf-5 disulfiram treatment gave rise to a metabolite found to be glycine betaine aldehyde. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.05.002
• 作为产物：
  描述：

  3,4-二甲氧基肉桂酸 在 氯化亚砜 、 盐酸羟胺 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 3,4-dimethoxycinnamohydroxamic acid
  参考文献：
  名称：

  Syntheses and anti-inflammatory and analgesic activities of hydroxamic acids and acid hydrazides.

  摘要：

  根据普遍接受的观点，铜离子参与了炎症的发生，因此合成了来自各种取代肉桂酸和氢肉桂酸的羟肟酸和酸肼，期望它们能与铜离子形成配位化合物，并通过卡拉胶诱导的大鼠爪肿胀实验评估其抗炎活性，通过苯醌扭动法评估其镇痛活性。部分合成的化合物表现出这两种活性，3-(3, 4-二甲氧基苯基)丙氢羟肟酸及其锌配合物的活性超过阿司匹林。羟肟酸衍生物的铜(II)配合物被合成，并根据元素分析、分子量测定和磁性测试结果推测其具有聚合结构。

  DOI：

  10.1248/cpb.31.2810

文献信息

• Syntheses and anti-inflammatory and analgesic activities of hydroxamic acids and acid hydrazides.
  作者：KUNIYOSHI TANAKA、KEIZO MATSUO、AI NAKANISHI、TOSHIKO HATANO、HISAKO IZEKI、YOKO ISHIDA、WASUKE MORI

  DOI：10.1248/cpb.31.2810

  日期：——

  On the basis of the generally accepted view that copper ions take part in the occurrence of inflammation, hydroxamic acids and acid hydrazides derived from various substituted cinnamic acids and hydrocinnamic acids, which were expected to chelate with copper ions, were synthesized and evaluated for anti-inflammatory activity by the carrageenin-induced rat paw edema assay and for analgesic activity by the phenylquinone writhing method in mice. Some of the synthesized compounds exhibited both activities, and 3-(3, 4-dimethoxyphenyl)propiohydroxamic acid and its Zn complex were more active than aspirin. The Cu (II) complexes of hydroxamic acid derivatives were synthesized and were assumed to have polymeric structures from the results of elemental analysis, molecular weight measurement and determination of magnetic susceptibility.

  根据普遍接受的观点，铜离子参与了炎症的发生，因此合成了来自各种取代肉桂酸和氢肉桂酸的羟肟酸和酸肼，期望它们能与铜离子形成配位化合物，并通过卡拉胶诱导的大鼠爪肿胀实验评估其抗炎活性，通过苯醌扭动法评估其镇痛活性。部分合成的化合物表现出这两种活性，3-(3, 4-二甲氧基苯基)丙氢羟肟酸及其锌配合物的活性超过阿司匹林。羟肟酸衍生物的铜(II)配合物被合成，并根据元素分析、分子量测定和磁性测试结果推测其具有聚合结构。
• Cinnamohydroxamic acids
  申请人：Ortho Pharmaceutical Corporation

  公开号：US04820828A1

  公开（公告）日：1989-04-11

  The present invention relates to cinnamohydroxamic acids. These compounds inhibit 5-lipoxygenase and are useful as bronchodilators.

  本发明涉及肉桂羟肟酸。这些化合物抑制5-脂氧合酶并且作为支气管扩张剂有用。
• Chemical intervention in bacterial lignin degradation pathways: Development of selective inhibitors for intradiol and extradiol catechol dioxygenases
  作者：Paul D. Sainsbury、Yelena Mineyeva、Zoe Mycroft、Timothy D.H. Bugg

  DOI：10.1016/j.bioorg.2015.05.002

  日期：2015.6

  Bacterial lignin degradation could be used to generate aromatic chemicals from the renewable resource lignin, provided that the breakdown pathways can be manipulated. In this study, selective inhibitors of enzymatic steps in bacterial degradation pathways were developed and tested for their effects upon lignin degradation. Screening of a collection of hydroxamic acid metallo-oxygenase inhibitors against two catechol dioxygenase enzymes, protocatechuate 3,4-dioxygenase (3,4-PCD) and 2,3-dihydroxyphenylpropionate 1,2-dioxygenase (MhpB), resulted in the identification of selective inhibitors D13 for 3,4-PCD (IC50 15 mu M) and D3 for MhpB (IC50 110 mu M). Application of D13 to Rhodococcus jostii RHA1 in minimal media containing ferulic acid led to the appearance of metabolic precursor protocatechuic acid at low concentration. Application of 1 mM disulfiram, an inhibitor of mammalian aldehyde dehydrogenase, to R. jostii RHA1, gave rise to 4-carboxymuconolactone on the beta-ketoadipate pathway, whereas in Pseudomonas fluorescens Pf-5 disulfiram treatment gave rise to a metabolite found to be glycine betaine aldehyde. (C) 2015 Elsevier Inc. All rights reserved.