N-(3,5-二硝基苯甲酰基)苯丙氨酸甲酯 | 69632-44-6

• 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
• 中文名称: N-(3,5-二硝基苯甲酰基)苯丙氨酸甲酯
• 英文名称: N-(3,5-dinitrobenzoyl)phenylalanine methyl ester
• 英文别名: methyl (2S)-2-[(3,5-dinitrobenzoyl)amino]-3-phenylpropanoate
• CAS: 69632-44-6
• 化学式: C₁₇H₁₅N₃O₇
• 分子量: 373.322
• InChiKey: BDWRHHADIGLFLL-HNNXBMFYSA-N

物化性质

• 沸点：
  553.2±50.0 °C(Predicted)
• 密度：
  1.395±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(3,5-二硝基苯甲酰基)苯丙氨酸甲酯 在 sodium hydroxide 、 水 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 生成 N-(3,5-dinitrobenzoyl)-L-phenylalanine
  参考文献：
  名称：

  Design, synthesis and SAR studies of tripeptide analogs with the scaffold 3-phenylpropane-1,2-diamine as aminopeptidase N/CD13 inhibitors

  摘要：

  Aminopeptidase N (APN), belonged to metalloproteinase, is an essential peptidase involved in the process of tumor invasion and metastasis. A series of tripeptide analogs with the scaffold 3-phenylpropane-1,2-diamine were designed, synthesized and evaluated for their ability to inhibit APN. Preliminary activity evaluation showed that most of target compounds possessed potent inhibitory activities against APN. With in this series, compound A6 and B6 exhibited good potency with the IC50 values of 8.8 +/- 1.3 mu M and 8.6 +/- 1.1 mu M, respectively. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.034
• 作为产物：
  描述：

  3,5-二硝基苯甲酸 、 L-苯丙氨酸甲酯 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 N-(3,5-二硝基苯甲酰基)苯丙氨酸甲酯
  参考文献：
  名称：

  Design, synthesis and SAR studies of tripeptide analogs with the scaffold 3-phenylpropane-1,2-diamine as aminopeptidase N/CD13 inhibitors

  摘要：

  Aminopeptidase N (APN), belonged to metalloproteinase, is an essential peptidase involved in the process of tumor invasion and metastasis. A series of tripeptide analogs with the scaffold 3-phenylpropane-1,2-diamine were designed, synthesized and evaluated for their ability to inhibit APN. Preliminary activity evaluation showed that most of target compounds possessed potent inhibitory activities against APN. With in this series, compound A6 and B6 exhibited good potency with the IC50 values of 8.8 +/- 1.3 mu M and 8.6 +/- 1.1 mu M, respectively. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.034

文献信息

• Preparation of Two New Diasteromeric Chiral Stationary Phases Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid and (R)- or (S)-1-(1-Naphthyl)ethylamine and Chiral Tethering Group Effect on the Chiral Recognition
  作者：Rajalingam Agneeswari、Ji Sung、Eun Jo、Hee Jeon、Vellaiappillai Tamilavan、Myung Hyun

  DOI：10.3390/molecules21081051

  日期：——

  effect on the chiral recognition while (S)-1-(1-naphthyl)ethylamine and (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid constituting CSP 2 were concluded to show an uncooperative (“mismatched”) effect on the chiral recognition. From these results, it was concluded that (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid can be successfully used as a chiral tethering group for the preparation of new CSPs

  基于 (+)-(18-crown-6)-2,3,11,12-四羧酸作为手性束缚基团和 Π-碱性手性单元（如 (R)）的两种新型非对映体手性固定相 (CSP)制备-1-(1-萘基)乙胺(CSP 1)或(S)-1-(1-萘基)乙胺(CSP 2)。使用 20% 异丙醇/己烷作为常规流动相，将这两种 CSP 应用于 N-(3,5-二硝基苯甲酰基)-1-苯基烷基胺和 N-(3,5-二硝基苯甲酰基)-α-氨基酸衍生物的对映体分离阶段。为了阐明两个手性单元对手性识别的影响，将两种CSP的手性识别能力相互比较，并与基于（R）-1-（1-萘基）的CSP（CSP 3）的手性识别能力进行比较乙胺。从色谱手性识别结果来看，(R)-1-(1-萘基)乙胺和(+)-(18-crown-6)-2,3,11，构成 CSP 1 的 12-四羧酸显示出对手性识别的协同（“匹配”）效应，而 (S)-1-(1-萘基) 乙胺和 (+)-(18-crown-6)-2构成
• Chiral separation on various modified amino alcohol-derived HPLC chiral stationary phases
  作者：Jeongjae Yu、Jung Mi Lee、Jae Jeong Ryoo

  DOI：10.1002/chir.22576

  日期：2016.4

  3,5‐Dinitrobenzoyl chloride was previously used for the preparation of (R)‐phenylglycinol‐ and (S)‐leucinol‐derived chiral stationary phases. In this study, 3,5‐bis(trifluoromethyl)benzoyl chloride, 2‐furoyl chloride, 2‐theonyl chloride, 10,11‐dihydro‐5H‐dibenzo[b,f]azepine‐5‐carbonyl chloride, diphenylcarbamoyl chloride, and 1‐adamantanecarbonyl chloride were used to prepare six new phenylglycinol‐derived

  以前曾使用3,5-二硝基苯甲酰氯制备（R）-苯基甘氨醇和（S）-亮氨醇衍生的手性固定相。在这项研究中，3,5-双（三氟甲基）苯甲酰氯，2-糠酰氯，2-theonyl chloride，10,11-dihydro-5H-dibenzo [b，f] azepine-5-羰基氯，二苯基氨基甲酰氯和1-金刚烷羰基氯化物用于制备6种新的苯甘醇衍生的手性固定相（CSP）和5种新的亮白酚衍生的CSP。使用这11种CSP进行了9种π-酸性氨基酸衍生物和5种π-碱性化合物的手性分离，并比较了分离结果。金刚烷基衍生的CSP表现出良好的分离性。手性28：276–281，2016。©2016 Wiley Periodicals，Inc.
• Enantioselective Hydrolysis of N-Acylated α-Amino Esters at a Biphasic Interface:  Tandem Reaction Kinetic Resolution Using a Chiral Complexing Agent
  作者：Seth E. Snyder、William H. Pirkle

  DOI：10.1021/ol026517s

  日期：2002.9.1

  Highly enantioselective hydrolytic kinetic resolutions of esters derived from N-acylated alpha-amino acids proceed rapidly at hydorcarbon/water interfaces in the presence of a proline-derived chiral selector. When performed in tandem with an enantioselective biphasic esterification reaction, esters of 100% enantiomeric excess are obtained.
• SALVADORI, P.;PINI, D.;ROSINI, C.;UCCELLO-BARRETTA, G.;BERTUCCI, C., J. CHROMATOGR., 450,(1988) N 2, C. 163-168
  作者：SALVADORI, P.、PINI, D.、ROSINI, C.、UCCELLO-BARRETTA, G.、BERTUCCI, C.

  DOI：——

  日期：——
• Design, synthesis and SAR studies of tripeptide analogs with the scaffold 3-phenylpropane-1,2-diamine as aminopeptidase N/CD13 inhibitors
  作者：Luqing Shang、Hao Fang、Huawei Zhu、Xuejian Wang、Qiang Wang、Jiajia Mu、Binghe Wang、Shiroh Kishioka、Wenfang Xu

  DOI：10.1016/j.bmc.2009.02.034

  日期：2009.4

  Aminopeptidase N (APN), belonged to metalloproteinase, is an essential peptidase involved in the process of tumor invasion and metastasis. A series of tripeptide analogs with the scaffold 3-phenylpropane-1,2-diamine were designed, synthesized and evaluated for their ability to inhibit APN. Preliminary activity evaluation showed that most of target compounds possessed potent inhibitory activities against APN. With in this series, compound A6 and B6 exhibited good potency with the IC50 values of 8.8 +/- 1.3 mu M and 8.6 +/- 1.1 mu M, respectively. (c) 2009 Elsevier Ltd. All rights reserved.