DL-4-(4-nitrophenyl)-2-aminobutanoic acid | 139973-76-5

• 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: DL-4-(4-nitrophenyl)-2-aminobutanoic acid
• 英文别名: DL-2-Amino-4-(4-nitrophenyl)buttersaeure；2-amino-4-(4'-nitrophenyl)butyric acid；2-amino-4-(4-nitrophenyl)butyric acid；2-amino-4-(4-nitro-phenyl)-butyric acid；2-Amino-4-(4-nitro-phenyl)-buttersaeure；4-Nitro-DL-homophenylalanine；2-amino-4-(4-nitrophenyl)butanoic acid
• CAS: 139973-76-5
• 化学式: C₁₀H₁₂N₂O₄
• 分子量: 224.216
• InChiKey: YLRIJQHXHLYYBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  DL-4-(4-nitrophenyl)-2-aminobutanoic acid 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 氢气 作用下， 以 乙醇 为溶剂， 25.0~70.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 1-methyl-4-[(4-anilino)ethyl]imidazolidine-2,5-dione
  参考文献：
  名称：

  一种新型的2,5-取代的色胺衍生物作为血管5HT1B / 1D受体拮抗剂。

  摘要：

  描述了在血管5HT1B样受体上一系列新的2,5-取代的色胺衍生物的设计，合成和活性。在对2-取代基，特别是对亚甲基或乙烯连接的5-侧链进行各种修饰之后，已经提出了5HT1B-样受体的几个重要的辅助结合位点。基于5HT1B样受体的拟药模型对新分子的仔细设计导致发现乙基3- [2-（二甲基氨基）乙基] -5- [2-（2,5-二氧代-1-咪唑啉基] ）[乙基] -1H-吲哚-2-羧酸酯（40），一种高效，沉默，竞争和选择性的拮抗剂，仅对血管5HT1B样受体具有亲和力。2酯取代基大小的变化对5HT1B样受体和其他受体的亲和力有重要影响。在5侧链的杂环中谨慎地放置羰基取代基对于5HT2A和其他受体的良好亲和力和选择性至关重要。确定了几个关键的结构和电子特征，这些特征对基于色胺的系列药物产生拮抗作用至关重要。为了实现拮抗作用，缺电子的吲哚环系统似乎是必不可少的，这是通过在吲哚环的2-位包含吸电子基团

  DOI：

  10.1021/jm9605849
• 作为产物：
  描述：

  2-(4-硝基苯基)乙酰氯 在 盐酸 、 锂硼氢 、 四溴化碳 、 sodium ethanolate 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 溶剂黄146 、 苯 为溶剂， 反应 7.5h， 生成 DL-4-(4-nitrophenyl)-2-aminobutanoic acid
  参考文献：
  名称：

  Herbert, Richard B.; Knaggs, Andrew R., Journal of the Chemical Society. Perkin transactions I, 1992, # 1, p. 109 - 114

  摘要：

  DOI：

文献信息

• Computer-Aided Design and Synthesis of 5-Substituted Tryptamines and Their Pharmacology at the 5-HT1D Receptor: Discovery of Compounds with Potential Anti-Migraine Properties
  作者：Janet Buckingham、Robert C. Glen、Alan P. Hill、Richard M. Hyde、Graeme R. Martin、Alan D. Robertson、John A. Salmon、Patrick M. Woollard

  DOI：10.1021/jm00018a016

  日期：1995.9

  pharmacophore hypothesis which was consistent with the affinity and selectivity measured at 5-HT1D and 5-HT2A receptors. This pharmacophore is composed of a protonated amine site, an aromatic site, a hydrophobic pocket, and two hydrogen-bonding sites. A "selectivity site" was also identified which, if occupied, induced sensitivity for 5-HT1D over 5-HT2A in this series of molecules. The development and use

  描述了一系列对5-HT1D具有药理活性的新型5-取代色胺和其他单胺受体的设计和合成。合成了N位和C位连接的（主要是乙内酰脲）类似物在5位上的结构修饰，并利用其药理活性推导了5-HT1D和5-HT2A受体亚型的显着空间和静电需求。计算了活性分子的构象，当它们重叠时，提出了药效基团假说，该假说与在5-HT1D和5-HT2A受体上测得的亲和力和选择性一致。该药效团由质子化的胺位点，芳族位点，疏水口袋和两个氢键位组成。还确定了一个“选择性位点”，如果被占领，在这一系列分子中对5-HT1D的敏感性高于5-HT2A。描述了药效团模型在化合物设计中的开发和使用。另外，讨论了有效口服吸收所需的分子大小和疏水性的物理化学约束。利用药效团模型结合分子大小和log DpH7.4的物理化学约束条件，导致了311C90（6）的发现，311C90是一种新型的选择性5-HT1D激动剂，具有良好的口服吸收能力，可用于治疗偏头痛。
• Bimodal ligands with macrocyclic and acyclic binding moieties, complexes and compositions thereof, and methods of using
  申请人：Chong Hyun-soon

  公开号：US09115094B2

  公开（公告）日：2015-08-25

  Substituted 1,4,7-triazacyclononane-N,N′,N″-triacetic acid and 1,4,7,10-tetraazacyclcododecane-N,N′,N″,N′″-tetraacetic acid compounds with a pendant amino or hydroxyl group, metal complexes thereof, compositions thereof, and methods of making and use in diagnostic imaging and treatment of cellular disorders.

  用带有氨基或羟基的1,4,7-三氮杂环壬烷-N,N′,N″-三乙酸和1,4,7,10-四氮杂环十二烷-N,N′,N″,N′″-四乙酸化合物替代，以及它们的金属配合物、组合物、制备方法以及在诊断成像和治疗细胞疾病中的应用。
• Synthesis and serotonergic activity of a series of 2-(N-benzyl)carboxamido-5-substituted-N,N-dimethyltryptamine derivatives: novel antagonists for the vascular 5-HT1B-like receptors
  作者：Gerard P. Moloney、Graeme R. Martin、Neil Mathews、Heather Hobbs、Susan Dodsworth、Pang Yih Sang、Cameron Knight、Miles Maxwell、Robert C. Glen

  DOI：10.1039/a903141c

  日期：——

  The synthesis and vascular 5-HT1B-like receptor activity of a novel series of 2-(N-benzyl)carboxamido-5-substituted-N,N-dimethyltryptamine derivatives is described. Modifications to the 5-ethylene linked heterocycle are explored. Compounds such as N-benzyl-5-[2-(phthalimido)ethyl]-3-[2-(dimethylamino)ethyl]-1H-indole-2-carboxamide 22 (pKB = 7.33), the 2-aminobenzyl analogue 24 (pKB = 7.19), which both contain a phthalimide group, and N-benzyl-5-[2-(1-benzyl-2,5-dioxoimidazolidin-4-yl)ethyl]-3-[2-(dimethylamino)ethyl]-1H-indole-2-carboxamide 81 (pKB = 7.05), which incorporates an N-benzylhydantoin moiety, have good 5-HT1B-like affinity and indicate that there may be a hydrophobic binding pocket within the vascular 5-HT1B-like receptor previously not considered. Compounds including N-benzyl-3-[2-(dimethylamino)ethyl]-5-[2-(2,4-dioxo-1,3-thiazolidinyl)ethyl]-1H-indole-2-carboxamide 39 (pKB = 7.35) and the dimethyl analogue 46 (pKB = 7.48) which contain a 2,4-thiazolidinedione moiety have good vascular 5-HT1B-like receptor affinity and show that the sulfur atom is well tolerated. Compound 61 which includes a methylsulfonyl substituent on the 1-nitrogen of the hydantoin ring system has the highest recorded 5-HT1B-like affinity for this series (pKB = 7.54) and it is proposed that this functional group can interact with a secondary hydrogen bonding region within the receptor. Compounds 22, 24, 39, 46, 61 and 81 also exhibited good selectivity over the α1-adrenoceptors. The most selective compound from this series is 46 which contains a 5,5-dimethylthiazolidine-2,4-dione group and which is 66-fold selective over the α1-adrenoceptors. This finding is consistent with the previous discovery that 5,5-dimethyl substitution on the hydantoin group in a related series of compounds afforded superior selectivity for 5-HT1B-like receptors over α1-adrenoceptors and other 5-HT receptors, in particular 5-HT2A receptors, relative to unsubstituted hydantoin analogues. The selectivity of these compounds for the vascular 5-HT1B-like receptor is discussed. Structure–activity relationship indicated a significant steric requirement of the 5-HT1B-like receptor subtype. Potential modes of binding for several of the compounds to a vascular 5-HT1B-like receptor pharmacophore model are also proposed.

  0)。
• ANTIHYPERTENSIVE AGENTS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND PROCESSES FOR THE PREPARATION OF THE AGENTS AND COMPOSITIONS
  申请人：SCHERING CORPORATION

  公开号：EP0236307B1

  公开（公告）日：1991-04-17
• Davis et al., Journal of the Chemical Society, 1955, p. 890,894
  作者：Davis et al.

  DOI：——

  日期：——