4-吗啉-4-基-4-氧代丁酸 | 67900-19-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-吗啉-4-基-4-氧代丁酸
• 中文别名: 4-(4-吗啉基)-4-氧代丁酸
• 英文名称: 4-morpholino-4-oxobutanoic acid
• 英文别名: 3-Morpholinocarbonylpropionsaeure；3-morpholinocarbonylpropionic acid；4-Morpholin-4-yl-4-oxo-butyric acid；4-morpholin-4-yl-4-oxobutanoic acid
• CAS: 67900-19-0
• 化学式: C₈H₁₃NO₄
• mdl: MFCD00517698
• 分子量: 187.196
• InChiKey: OJFWUNYQLGJYEO-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °C(Solv: benzene (71-43-2))
• 沸点：
  420.3±40.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  4-吗啉-4-基-4-氧代丁酸 在 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 lithium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (2R)-3-(Morpholinocarbonyl)-2-(1-naphthylmethyl)-propionic acid
  参考文献：
  名称：

  Tanaka, Fujie; Node, Manabu; Tanaka, Kiyoshi, Journal of the American Chemical Society, 1995, vol. 117, # 49, p. 12159 - 12171

  摘要：

  DOI：
• 作为产物：
  描述：

  吗啉 、 戊二酸酐 以 二氯甲烷 为溶剂， 反应 5.0h， 以95%的产率得到4-吗啉-4-基-4-氧代丁酸
  参考文献：
  名称：

  Polycyclic aromatic compounds as anticancer agents: structure–activity relationships of chrysene and pyrene derivatives

  摘要：

  A large number of diamides and diamines were synthesized using 6-amino chrysene and 1-amino pyrene as starting materials. A structure-activity study with cis-platinum as internal control against animal and human tumor lines was carried out in vitro. This study indicated that the in vitro cytotoxicity toward these lines depends on the functionality present in the molecules. The diamino compounds were found to be more potent than the diamides, and these were equally active irrespective of the end heterocyclic group, whereas the activity of the diamides was strongly dependent on the terminal unit. In general, the diamides containing chrysene as the chromophore were more active than those with a pyrene ring. The size of the end heterocyclic ring, along with the nature of the spacer connecting the polycyclic ring to the heterocyclic ring, seemed to affect the biological activity in certain cell lines. Hemolysis experiments on a lead compound established that it had activities similar to those described for membrane-stabilizing agents. This agent also demonstrated the capacity to produce differentiation in leukemia cell lines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00297-2

文献信息

• Design, synthesis and anticancer activity of naphthoquinone derivatives
  作者：Xiao-bao Shen、Yang Wang、Xuan-zhen Han、Liang-quan Sheng、Fu-fang Wu、Xinhua Liu

  DOI：10.1080/14756366.2020.1740693

  日期：2020.1.1

  were designed and synthesised. With the help of reverse targets searching, anti-cancer activity was preliminarily evaluated, most of them are effective against some tumour cells, especially compound 12: 1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl-4-oxo-4-((4-phenoxyphenyl)amino) butanoate whose IC50 against SGC-7901 was 4.1 ± 2.6 μM. Meanwhile the anticancer mechanism

  摘要 基于萘醌部分的分子对接和药效团分析，总共设计和合成了23种化合物。借助反向靶标搜索，初步评估了其抗癌活性，其中大多数对某些肿瘤细胞有效，尤其是化合物12：1-（5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen -2-基）-4-甲基戊-3-烯-1-基-4-氧代-4-（（4-苯氧基苯基）氨基）丁酸酯，其对SGC-7901的IC 50为4.1±2.6μM。同时通过AnnexinV / PI染色，免疫荧光，Western印迹分析和分子对接研究了化合物12的抗癌机理。结果表明该化合物可能通过调节PI3K信号通路诱导细胞凋亡和细胞自噬。
• Synthesis, characterization, interaction with anionic dye, biodegradability, and antimicrobial activity of cationic surfactants: quaternary hydrazinium derivatives
  作者：Nora M. Hilal、Entsar. E. Badr、Elshimaa H. Gomaa、Eman M. Kandeel、Rabab A. Ismail、Entsar M. Ahmed

  DOI：10.1007/s13738-021-02247-3

  日期：2021.11

  'N'dimethyl-4-morpholino-4-oxobutanoylhydrazinium iodide (10a–12a) and N'alkyl N', N'dimethyl-4-piperidino-4-oxobutanoylhydrazinium iodide (10b–12b) of quaternary hydrazinium moieties in hydrophilic parts was synthesized. These quaternary hydrazinium surfactants were obtained using a two-step reaction scheme, starting from ring opening of succinic anhydride with a base (morpholine, piperidine), followed by

  一种新型的阳离子表面活性剂 N'烷基 N,'N'二甲基-4-吗啉-4-氧代丁酰肼碘化物 ( 10a–12a ) 和 N'烷基 N', N'二甲基-4-哌啶基-4-氧代丁酰肼碘化物 ( 10b) –12b ) 在亲水部分合成了季肼部分。这些季肼表面活性剂是使用两步反应方案获得的，从琥珀酸酐与碱（吗啉、哌啶）开环开始，然后用水合肼氨解，然后用烷基溴（RBr）烷基化氨基，具有不同的疏水链长度（R、C 12 H 25、C 14 H 29和 C 16 H 37)，最后是仲氨基被两摩尔碘甲烷季铵化。表面活性剂的化学成分通过FTIR、1 HNMR、质谱和元素分析进行​​分析。通过表面计算获得了多种表面活性特性，包括 CMC、γcmc、CMC/C 20、Γ max、pC 20、A min和Π cmc。这些表面特性和泡沫稳定性取决于疏水链的性质。初步结果表明，整个 CH 2的升级脂肪链中的基团和吗啉或哌啶环降低了
• Discovery and Characterization of Biased Allosteric Agonists of the Chemokine Receptor CXCR3
  作者：Lampros Milanos、Regine Brox、Theresa Frank、Gašper Poklukar、Ralf Palmisano、Reiner Waibel、Jürgen Einsiedel、Maximilian Dürr、Ivana Ivanović-Burmazović、Olav Larsen、Gertrud Malene Hjortø、Mette Marie Rosenkilde、Nuska Tschammer

  DOI：10.1021/acs.jmedchem.5b01965

  日期：2016.3.10

  of G proteins. A subtle structural change (addition of a methoxy group, 14 (FAUC1104)) led to a contrasting biased allosteric partial agonist that activated solely G proteins, induced chemotaxis, but failed to induce receptor internalization or β-arrestin 2 recruitment. Concomitant structure–activity relationship studies indicated very steep structure–activity relationships, which steer the ligand

  在这项工作中，我们报告了包含四氢异喹啉羧酰胺核心的CXCR3的独特强偏置变构激动剂的设计，合成和详细的功能表征。化合物11（FAUC1036）是CXCR3的第一个强烈偏向的变构激动剂，可选择性诱导弱的趋化作用，并导致受体内化和β-arrestin2募集，其效力与趋化因子CXCL11相当，而没有任何G蛋白的活化。细微的结构变化（添加甲氧基14（FAUC1104））导致了一种对比偏向的变构部分激动剂，该激动剂仅激活G蛋白，诱导趋化性，但未能诱导受体内化或β-arrestin2募集。伴随的结构-活性关系研究表明，结构-活性之间的关系非常陡峭，从而引导了β-arrestin2和G蛋白途径之间的配体偏倚。总体而言，本文提供的信息为进一步开发和合理设计CXCR3的强偏置变构激动剂提供了强大的平台。
• [EN] AGONISTS OF THE CHEMOKINE RECEPTOR CXCR3<br/>[FR] AGONISTES DU RÉCEPTEUR DE CHIMIOKINE CXCR3
  申请人：FRIEDRICH-ALEXANDER-UNIVERSITÄT ERLANGEN-NÜRNBERG

  公开号：WO2017063910A1

  公开（公告）日：2017-04-20

  The present invention relates to agonists of the chemokine receptor CXCR3, methods of their synthesis and uses thereof.

  这项发明涉及趋化因子受体CXCR3的激动剂，其合成方法及其用途。
• Direct amide bond formation from carboxylic acids and amines using activated alumina balls as a new, convenient, clean, reusable and low cost heterogeneous catalyst
  作者：Sabari Ghosh、Asim Bhaumik、John Mondal、Amit Mallik、Sumita Sengupta (Bandyopadhyay)、Chhanda Mukhopadhyay

  DOI：10.1039/c2gc35880h

  日期：——

  For the first time, we have used activated alumina balls (3–5 mm diameter) for amide synthesis from carboxylic acids (unactivated) and amines (unactivated) under neat reaction conditions that produce no toxic by-products and has the advantages of being low-cost, easily available, heterogeneous, reusable and environmentally benign with no troublesome/hazardous disposal of the catalyst.

  我们首次使用活性氧化铝球（直径3–5毫米） 酰胺 合成自 羧酸 （未激活）和 胺类 （未活化），在不产生有毒副产物的纯净反应条件下，具有低成本，易于获得，异构，可重复使用且对环境无害的优点，而不会造成麻烦/危险的处置 催化剂。