p-nitrophenylalanine tert-butyl ester | 116366-32-6

• 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
• 英文名称: p-nitrophenylalanine tert-butyl ester
• 英文别名: 4-nitro-L-phenylalanine t-butyl ester；L-4-nitrophenylalanine tert-butyl ester；(p-nitrophenylalanine)-t-butyl ester；H-Phe(p-NO2)OtBu；t-butyl (2S)-2-amino-3-(4-nitrophenyl)propionate；L-4'-nitrophenylalanine t-butyl ester；tert-butyl (2S)-2-amino-3-(4-nitrophenyl)propanoate
• CAS: 116366-32-6
• 化学式: C₁₃H₁₈N₂O₄
• 分子量: 266.297
• InChiKey: WFXHVZZCTZMYSA-NSHDSACASA-N

物化性质

• 沸点：
  385.2±27.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  p-nitrophenylalanine tert-butyl ester 在 盐酸 、 potassium fluoride on Celite 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 5.0h， 生成 tert-butyl (2S)-2-[[(2S)-1-[2-(3-methoxyphenyl)-2-oxoethyl]piperidine-2-carbonyl]amino]-3-(4-nitrophenyl)propanoate
  参考文献：
  名称：

  Design and synthesis of novel FKBP inhibitors

  摘要：

  Small molecule FKBP inhibitors were prepared with inhibitory activity ranging from micromolar to nanomolar. The design of these inhibitors derives from a structural analysis of the substrates for FKBP and cyclophilin. As a consequence of this analysis two key observations were made, namely: (1) amino ketone moieties are suitable as FKBP recognition elements at the P1-P1' site and (2) the P3'-P4' site will accept a trans-olefin as a suitable mimetic of a peptide moiety. The preparation of these non-peptide inhibitors is readily accomplished by a protocol which includes the synthesis of chiral propargylic amines and their subsequent conversion into vinyl zirconium reagents.

  DOI：

  10.1021/jm00101a005
• 作为产物：
  描述：

  Fmoc-对硝基-L-苯丙氨酸 在 二乙胺 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 48.0h， 生成 p-nitrophenylalanine tert-butyl ester
  参考文献：
  名称：

  Toward a Rational Design of Peptide Inhibitors of Ribonucleotide Reductase:  Structure−Function and Modeling Studies

  摘要：

  Mammalian ribonucleotide reductase, a chemotherapeutic target, has two subunits, mR1 and mR2, and is inhibited by AcF(1)TLDADF(7), denoted P7. P7 corresponds to the C-terminus of mR2 and competes with mR2 for binding to mR1. We report results of a structure-function analysis of P7, obtained using a new assay measuring peptide ligand binding to mR1, that demonstrate stringent specificity for Phe at F-7, high specificity for Phe at F-1, and little specificity for the N-acyl group. They support a structural model in which the dominant interactions of P7 occur at two mR1 sites, the F-1 and F-7 subsites. The model is constructed from the structure of Escherichia colt R1 (eR1) complexed with the C-terminal peptide from eR2, aligned sequences of mR1 and eR1, and the trNOE-derived structure of mR1-bound P7. Comparison of this model with similar models constructed for mR1 complexed with other inhibitory ligands indicates that increased F-1 subsite interaction can offset lower F-7 subsite interaction and suggests strategies for the design of new, higher affinity inhibitors.

  DOI：

  10.1021/jm000335r

文献信息

• Multimeric VLA-4 antagonists comprising polymer moieties
  申请人：Konradi W. Andrei

  公开号：US20060013799A1

  公开（公告）日：2006-01-19

  Disclosed are conjugates which bind VLA-4. Certain of these conjugates also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such conjugates are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The conjugates can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

  公开的是结合VLA-4的偶联物。其中一些偶联物还能抑制白细胞粘附，特别是VLA-4介导的白细胞粘附。这类偶联物可用于治疗哺乳动物患者，如人类的炎症性疾病，例如哮喘、阿尔茨海默病、动脉粥样硬化、艾滋病痴呆、糖尿病、炎症性肠病、类风湿性关节炎、组织移植、肿瘤转移和心肌缺血。这些偶联物还可用于治疗炎症性脑病，如多发性硬化症。
• Pyrimidine hydantoin analogues which inhibit leukocyte adhesion mediated by VLA-4
  申请人：Konradi W. Andrei

  公开号：US20050261324A1

  公开（公告）日：2005-11-24

  Disclosed are compounds which bind VLA-4 and/or LPAM-1. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4 and/or LPAM-1. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

  披露了与VLA-4和/或LPAM-1结合的化合物。其中某些化合物还能抑制白细胞粘附，尤其是VLA-4和/或LPAM-1介导的白细胞粘附。这类化合物可用于治疗哺乳动物患者，如人类的炎症性疾病，例如哮喘、阿尔茨海默病、动脉粥样硬化、艾滋病痴呆、糖尿病、炎症性肠病、类风湿性关节炎、组织移植、肿瘤转移和心肌缺血。这些化合物也可用于治疗炎症性脑病，如多发性硬化症。
• ANTI-ALPHAVBETA1 INTEGRIN COMPOUNDS AND METHODS
  申请人：The Regents of the University of California

  公开号：US20160376266A1

  公开（公告）日：2016-12-29

  Provided herein, inter alia, are methods and compositions for inhibiting αvβ1 integrin and for treating fibrosis.

  本文提供了抑制αvβ1整合素和治疗纤维化的方法和组合物。
• Selective inhibition of human inducible nitric oxide synthase by<i>S</i>-alkyl-<scp>L</scp>-isothiocitrulline-containing dipeptides
  作者：Jung-Min Park、Tsunehiko Higuchi、Kazuya Kikuchi、Yasuteru Urano、Hiroyuki Hori、Takeshi Nishino、Junken Aoki、Keizo Inoue、Tetsuo Nagano

  DOI：10.1038/sj.bjp.0704023

  日期：2001.4

  The aim of this study was to investigate the structure-activity relationship of S-alkyl-L-isothiocitrulline-containing dipeptides towards three partially purified recombinant human nitric oxide synthase (NOS) isozymes, as well as the effects of these compounds on cytokine-induced NO production by human DLD-1 cells. In an in vitro assay, S-methyl-L-isothiocitrulline (L-MIT) was slightly selective for

  本研究的目的是研究含S-烷基-L-异硫瓜氨酸二肽对三种部分纯化的重组人一氧化氮合酶（NOS）同工酶的构效关系，以及这些化合物对细胞因子诱导的影响。人类 DLD-1 细胞产生 NO。在体外测定中，S-甲基-L-异硫瓜氨酸 (L-MIT) 对人神经元 NOS (nNOS) 的选择性略强于诱导型 (iNOS) 或内皮型 (eNOS) 同工酶，但疏水性 L-氨基的组合酸（L-Phe、L-Leu 或 L-Trp）与 L-MIT 显着改变了抑制模式，产生选择性 iNOS 抑制剂。在 L-MIT-L-Phe (MILF) 芳环的对位引入羟基、硝基、氨基或甲氧基会降低选择性和抑制效力。更长或更大的 S-烷基也会降低选择性和效力。Dixon 分析表明所有二肽都是人 NOS 三种亚型的竞争性抑制剂。酶时程曲线表明 MILF 是人 iNOS 的缓慢结合抑制剂。这些结果表明，人NOS同工酶在靠近L-精氨酸C末端结
• Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts
  作者：Jordi Rull、José Juan Jara、Rosa M. Sebastián、Adelina Vallribera、Carmen Nájera、Jean-Pierre Majoral、Anne-Marie Caminade

  DOI：10.1002/cctc.201600283

  日期：2016.6.21

  The asymmetric alkylation of a glycinate Schiff base with benzyl bromide is used as a benchmark reaction, and the dendrimeric catalyst that contains an allyl group on the O‐9 hydroxy group of the cinchonine units is the most active. The recovery and reuse of the catalyst are possible for five consecutive runs without loss of activity and with only a slight decrease in enantioselectivity. If other electrophiles

  制备了四种新的磷树枝状相转移催化剂，该催化剂在通过奎宁环烷基N原子的季铵化反应获得的表面上包含12（+）-金鸡尼盐。甘氨酸Schiff碱与苄基溴的不对称烷基化被用作基准反应，并且在辛可宁单元的O-9羟基上含有烯丙基的树枝状催化剂最为活跃。催化剂的回收和再利用可以连续进行五次，而不会损失活性，对映选择性仅略有降低。如果使用其他亲电试剂，则取代的苄基溴化物要比其他活化的烷基溴化物得到更好的结果，从而得到相应的R氨基酸衍生物。将这些结果与先前报道的类似金鸡铵盐的结果进行比较，结果表明，对于这种类型的有机催化，树状大分子可能比其他聚合物有更好的支持。