(S)-4-硝基苯丙氨酸甲酯 | 81677-60-3

• 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: (S)-4-硝基苯丙氨酸甲酯
• 英文名称: (L)-p-Nitrophenylalanine methyl ester
• 英文别名: (S)-methyl 2-amino-3-(4-nitrophenyl)propanoate；4-nitrophenylalanine methyl ester；methyl (2S)-2-amino-3-(4-nitrophenyl)propanoate
• CAS: 81677-60-3
• 化学式: C₁₀H₁₂N₂O₄
• 分子量: 224.216
• InChiKey: FUFUQQWIXMPZFU-VIFPVBQESA-N

物化性质

• 沸点：
  360.0±27.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

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：
  98.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-硝基苯丙氨酸甲酯 在 N-羟基丁二酰亚胺 、 水 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 lithium hydroxide 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 N-(3-(4-(5-(1,2-dithiolan-3-yl)pentanamido)phenyl)-1-((3,4-dimethoxyphenylethyl)-amino)-1-oxopropan-2-yl)-4-chlorobenzamide
  参考文献：
  名称：

  Enhancing Cell Recognition by Scrutinizing Cell Surfaces with a Nanoparticle Array

  摘要：

  We report a dual-ligand nanoparticle array approach for discerning cells that have different surface receptor profiles surrounding a common primary receptor expressed at high or low levels. The achieved differentiation provides nanoparticles the ability for potential applications in treatment of patients at a personalized medicine level for drug delivery and radiation therapy with a much better safety profile.

  DOI：

  10.1021/ja108527y
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 在 硫酸 、 硝酸 作用下， 反应 1.0h， 生成 (S)-4-硝基苯丙氨酸甲酯
  参考文献：
  名称：

  Design and synthesis of calcium responsive magnetic resonance imaging agent: Its relaxation and luminescence studies

  摘要：

  Calcium concentration modulation both inside and outside cell is of considerable interest for nervous system function in normal and pathological conditions. MRI has potential for very high spatial resolution at molecular/cellular level. Design, synthesis and evaluation of Gd-DO3A-AME-NPHE, a calcium responsive MRI contrast agent is presented. The probe is comprised of a Gd3+-DO3A core coupled to iminoacetate coordinating groups for calcium induced relaxivity switching. In the absence of Ca2+ ions, inner sphere water binding to the Gd-DO3A-AME-NPHE is restricted with longitudinal relaxivity, r(1) =4.37 mM(-1) s(-1) at 4.7 T. However, addition of Ca2+ triggers a marked enhancement in r(1) = 6.99 mM(-1) s(-1) at 4.7 T (60% increase). The construct is highly selective for Ca2+ over competitive metal ions at extracellular concentration. The r(1) is modulated by changes in the hydration number (0.2 to 1.05), which was confirmed by luminescence emission lifetimes of the analogous Eu3+ complex. T-1 phantom images establish the capability of complex of visualizing changes in [Ca2+] by MRI. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.046

文献信息

• [EN] A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS<br/>[FR] CONJUGUÉ D'UN ANALOGUE DE TUBULYSINE AVEC DES LIEURS RAMIFIÉS
  申请人：HANGZHOU DAC BIOTECH CO LTD

  公开号：WO2019127607A1

  公开（公告）日：2019-07-04

  The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.

  本发明涉及将一种管腔霉素类似物化合物与具有分支/侧链连接物的细胞结合分子结合，以实现结合物的更好传递和靶向治疗异常细胞。它还涉及一种将管腔霉素类似物分子与细胞结合配体结合的分支连接方法，以及在靶向治疗癌症、感染和自身免疫疾病中使用结合物的方法。
• PHENYLALANINE DIPEPTIDE DERIVATIVES, COMPOSITIONS AND USE THEREOF
  申请人：Liang Guangyi

  公开号：US20090247470A1

  公开（公告）日：2009-10-01

  Disclosed are a compound of formula I, stereoisomers, pharmaceutically acceptable salts or hydrates thereof, a pharmaceutical composition comprising the smae, a process for preparing the same and use thereof. The compound may also be used to prepare a medicament to treat viral infections, especially to prepare a medicament to treat hepatitis B virus and human immunodeficiency virus with little toxic side effects.

  公开了一种具有I式化合物、立体异构体、药学上可接受的盐或水合物的化合物，包括该化合物的药物组合物，制备该化合物的方法以及其用途。该化合物还可用于制备治疗病毒感染的药物，特别是用于制备治疗乙型肝炎病毒和人类免疫缺陷病毒的药物，具有较小的毒副作用。
• Fragment-Based Lead Generation of 5-Phenyl-1H-pyrazole-3-carboxamide Derivatives as Leads for Potent Factor Xia Inhibitors
  作者：Qunchao Wei、Zhichao Zheng、Shijun Zhang、Xuemin Zheng、Fancui Meng、Jing Yuan、Yongnan Xu、Changjiang Huang

  DOI：10.3390/molecules23082002

  日期：——

  FXIa is suggested as a major target for anticoagulant drug discovery because of reduced risk of bleeding. In this paper, we defined 5-phenyl-1H-pyrazole-3-carboxylic acid derivatives as privileged fragments for FXIa inhibitors’ lead discovery. After replacing the (E)-3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acrylamide moiety in compound 3 with 5-(3-chlorophenyl)-1H-pyrazole-3-carboxamide, we traveled from FXIa inhibitor3 to a scaffold that fused the privileged fragments into a pharmacophore for FXIa inhibitors. Subsequently, we synthesized and assessed the FXIa inhibitory potency of a series of 5-phenyl-1H-pyrazole-3-carboxamide derivatives with different P1, P1′ and P2′moiety. Finally, the SAR of them was systematically investigated to afford the lead compound 7za (FXIa Ki = 90.37 nM, 1.5× aPTT in rabbit plasma = 43.33μM) which exhibited good in vitro inhibitory potency against FXIa and excellent in vitro coagulation activities. Furthermore, the binding mode of 7za with FXIa was studied and the results suggest that the 2-methylcyclopropanecarboxamide group of 7za makes 2 direct hydrogen bonds with Tyr58B and Thr35 in the FXIa backbone, making 7za binds to FXIa in a highly efficient manner.

  FXIa被认为是抗凝药物发现的主要靶点，因为减少了出血风险。在这篇论文中，我们将5-苯基-1H-吡唑-3-羧酸衍生物定义为FXIa抑制剂的引物片段，用于引物发现。在将化合物3中的(E)-3-(5-氯-2-(1H-四唑-1-基)苯基)丙烯酰胺基团替换为5-(3-氯苯基)-1H-吡唑-3-羧酰胺后，我们从FXIa抑制剂3转变为将引物片段融合成FXIa抑制剂的药效团的支架。随后，我们合成并评估了一系列具有不同P1、P1'和P2'基团的5-苯基-1H-吡唑-3-羧酰胺衍生物的FXIa抑制活性。最后，对它们的结构活性关系进行了系统研究，得到了引物化合物7za（FXIa Ki = 90.37 nM，在兔血浆中1.5× aPTT = 43.33μM），该化合物表现出良好的体外抑制FXIa活性和优秀的体外凝血活性。此外，研究了7za与FXIa的结合方式，结果表明7za的2-甲基环丙烷甲酰胺基团与FXIa骨架中的Tyr58B和Thr35直接形成两个氢键，使7za以高效的方式结合到FXIa上。
• N-alkanoylphenylalanine derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US06455550B1

  公开（公告）日：2002-09-24

  Compounds of the formula: are disclosed which have activity as inhibitors of binding between VCAM-1 and cells expressing VLA-4. Such compounds are useful for treating diseases whose symptoms and/or damage are related to the binding of VCAM-1 to cells expressing VLA-4.

  揭示了具有以下化学式的化合物，这些化合物具有作为VCAM-1和表达VLA-4的细胞之间结合抑制剂的活性。这些化合物对于治疗那些症状和/或损害与VCAM-1与表达VLA-4的细胞结合有关的疾病是有用的。
• Cu/Mn Co-oxidized Cyclization for the Synthesis of Highly Substituted Pyrrole Derivatives from Amino Acid Esters: A Strategy for the Biomimetic Syntheses of Lycogarubin C and Chromopyrrolic Acid
  作者：Nini Zhou、Tao Xie、Lin Liu、Zhixiang Xie

  DOI：10.1021/jo500740w

  日期：2014.7.3

  An effective and concise approach to synthesis of tetrasubstituted pyrroles from readily available amino acid esters by the promotion of Cu(OAc)2 in conjunction with Mn(OAc)3 has been developed. This reaction proceeds through multiple dehydrogenations, deamination, and oxidative cyclization. This oxidized system tolerates substrates bearing various electron-donating or electron-withdrawing groups.

  通过促进Cu（OAc）2与Mn（OAc）3的结合，已经开发了一种有效，简洁的方法，可以从容易获得的氨基酸酯中合成四取代的吡咯。该反应通过多次脱氢，脱氨基和氧化环化而进行。这种氧化的系统可以承受带有各种给电子或吸电子基团的底物。用这种方法，已经有效地制备了几种天然产物的关键中间体，并且高效地完成了糖木蛋白C和色吡咯酸的全部合成。