3-bromo-N-ethylpropanamide | 21437-85-4

• 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
• 英文名称: 3-bromo-N-ethylpropanamide
• 英文别名: N-Ethyl-β-brom-propionamid；N-Ethyl-3-brompropionamid；3-bromo-propionic acid ethylamide；N-Aethyl-3-brom-propionamid；3-Brom-propionsaeure-aethylamid
• CAS: 21437-85-4
• 化学式: C₅H₁₀BrNO
• 分子量: 180.044
• InChiKey: SGEYBDFIAGICMY-UHFFFAOYSA-N

物化性质

• 沸点：
  289.7±23.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-N-ethylpropanamide 在 sodium hydroxide 作用下， 生成 N-ethyl 3-mercaptopropionamide
  参考文献：
  名称：

  Important Role of the 3-Mercaptopropionamide Moiety in Glutathione:  Promoting Effect on Decomposition of the Adduct of Glutathione with the Oxoammonium Ion of TEMPO

  摘要：

  Cyclic voltammetry of TEMPO in aqueous 0.1 M NaOH in the presence of glutathione (GSH) or cysteine (Cys) indicated the following points: (i) Both of the thiols rapidly formed adducts 3 with oxoammonium ion 1 anodically generated from TEMPO. (ii) 3 generated from GSH entered a succeeding reaction that generated N-oxide anion 2(-) (the reduced TEMPO). (iii) 3 produced from Cys remained intact over the time scale of voltammetry. A structural feature of GSH was considered to contribute to the observed behavior of this tripeptide. Possible structural features were evaluated by screening various thiols on the basis of whether they provided GSH-like voltammetric results. The 3-mercaptopropionamide group with an amide hydrogen in GSH was determined to be responsible for the observed difference between GSH and Cys. The likely function is to transform 3 from GSH into a 5-imino-1,2-oxathiolane intermediate, thereby releasing 2(-). Product analysis for reactions of model thiols representing GSH and Cys with 1 provided support for this argument and suggested that the reaction of GSH or Cys with 1 would produce the corresponding disulfides, regardless of whether a five-membered ring intermediate was formed. The proposed function of the 3-mercaptopropionamide moiety of GSH may provide useful insight for the molecular design of exogenous thiol compounds as novel drugs for the treatment of GSH-depletion-related disorders.

  DOI：

  10.1021/jo050783c
• 作为产物：
  描述：

  乙胺 、 3-溴丙酰氯 在 氯仿 作用下， 生成 3-bromo-N-ethylpropanamide
  参考文献：
  名称：

  Marini-Bettolo et al., Rendiconti - Istituto superiore di sanita, 1952, vol. 15, p. 844,845,849

  摘要：

  DOI：

文献信息

• Ketamine esters and amides as short-acting anaesthetics: Structure-activity relationships for the side-chain
  作者：Ivaylo V. Dimitrov、Martyn G. Harvey、Logan J. Voss、James W. Sleigh、Michael J. Bickerdike、William A. Denny

  DOI：10.1016/j.bmc.2019.02.010

  日期：2019.4

  N-Aliphatic ester analogues of the non-opioid ketamine (1) retain effective anaesthetic/analgesic properties while minimising ketamine's psychomimetic side-effects. We show that the anaesthetic/analgesic properties of these ester analogues depend critically on the length (from 2 to 4 carbons), polarity and steric cross-section of the aliphatic linker chain. More stable amide and ethylsulfone analogues generally

  非阿片类氯胺酮的N-脂族酯类似物（1）保留了有效的麻醉/镇痛特性，同时最大程度地降低了氯胺酮的拟精神病副作用。我们表明，这些酯类似物的麻醉/镇痛特性主要取决于脂肪族连接链的长度（2至4个碳），极性和空间截面。较稳定的酰胺和乙砜类似物通常显示较弱的麻醉/镇痛活性。化合物的麻醉/镇痛特性与其对N-甲基-d-天冬氨酸（NMDA）受体的结合亲和力之间没有相关性。
• 1-Phenylpyrazolo[3,4-d]pyrimidines as adenosine antagonists: the effects of substituents at C4 and C6
  作者：Mary Chebib、Ronald J. Quinn

  DOI：10.1016/s0968-0896(96)00240-4

  日期：1997.2

  Forty-two 1-phenyl-pyrazolo[3,4-d]pyrimidines substituted at C6 with thioethers containing distal amide substituents and substituted at C4 with thiol, thiomethyl or amino were synthesized and tested for adenosine A(1) and A(2a) receptor binding. Compared with a thiol at C4, both S-methylation and conversion to an amino resulted in increased affinity at both receptors with the C4 amino compounds having the highest affinity. The C-4 region of the receptor consists of an alkyl pocket containing a hydrogen-bonding site. The study established that for high affinity at both the A(1) and A(2a) adenosine receptors the distal amide should be separated from the C6 thiol by only one carbon. In this study, 2'-(4-amino-1-phenylpyrazolo[3,4-d]pyrimidin-6-ylthio)- N-ethyl-ethanamide (4b) had the highest affinity at the A(1) receptor with a K-i of 12.1 nM while 2'-(4-amino-1-phenylpyrazolo[3,4-d]pyrimidin-6-ylthio)ethanamide (4a) had the highest affinity at the A(2a) receptor with a K-i of 44.9 nM. (C) 1997, Elsevier Science Ltd.
• Marini-Bettolo et al., Rendiconti - Istituto superiore di sanita, 1952, vol. 15, p. 844,845,849
  作者：Marini-Bettolo et al.

  DOI：——

  日期：——
• Targeting new N-furfurylated 4-chlorophenyl-1,2,4-triazolepropionamide hybrids as potential 15-lipoxygenase inhibitors supported with <i>in vitro</i> and <i>in silico</i> studies
  作者：Muhammad Yasin、Wardah Shahid、Muhammad Ashraf、Muhammad Saleem、Saima Muzaffar、Aziz-ur-Rehman、Syeda Abida Ejaz、Hafiz Mohammad Kashif Mahmood、Keshab Bhattarai、Naheed Riaz

  DOI：10.1080/07391102.2022.2080765

  日期：——
• Important Role of the 3-Mercaptopropionamide Moiety in Glutathione:  Promoting Effect on Decomposition of the Adduct of Glutathione with the Oxoammonium Ion of TEMPO
  作者：Hatsuo Maeda、Hong-Yan Wu、Yuji Yamauchi、Hidenobu Ohmori

  DOI：10.1021/jo050783c

  日期：2005.10.1

  Cyclic voltammetry of TEMPO in aqueous 0.1 M NaOH in the presence of glutathione (GSH) or cysteine (Cys) indicated the following points: (i) Both of the thiols rapidly formed adducts 3 with oxoammonium ion 1 anodically generated from TEMPO. (ii) 3 generated from GSH entered a succeeding reaction that generated N-oxide anion 2(-) (the reduced TEMPO). (iii) 3 produced from Cys remained intact over the time scale of voltammetry. A structural feature of GSH was considered to contribute to the observed behavior of this tripeptide. Possible structural features were evaluated by screening various thiols on the basis of whether they provided GSH-like voltammetric results. The 3-mercaptopropionamide group with an amide hydrogen in GSH was determined to be responsible for the observed difference between GSH and Cys. The likely function is to transform 3 from GSH into a 5-imino-1,2-oxathiolane intermediate, thereby releasing 2(-). Product analysis for reactions of model thiols representing GSH and Cys with 1 provided support for this argument and suggested that the reaction of GSH or Cys with 1 would produce the corresponding disulfides, regardless of whether a five-membered ring intermediate was formed. The proposed function of the 3-mercaptopropionamide moiety of GSH may provide useful insight for the molecular design of exogenous thiol compounds as novel drugs for the treatment of GSH-depletion-related disorders.