L-phenylalanine n-butyl ester hydrochloride

• 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: L-phenylalanine n-butyl ester hydrochloride
• 英文别名: butyl (2S)-2-amino-3-phenylpropanoate;hydrochloride
• 化学式: C₁₃H₁₉NO₂*ClH
• 分子量: 257.76
• InChiKey: XHOFZUILKVVMBK-YDALLXLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.81
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  53.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-phenylalanine n-butyl ester hydrochloride 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Chiral Recognition of Carboxylates by a Static Library of Thiourea Receptors with Amino Acid Arms

  摘要：

  Chiral recognition is based on a large network of very subtle interactions whose outcome is difficult to predict. A combinatorial approach is therefore the most suitable to search for the most efficient receptor and obtain a structure-enantioselectivity correlation. We synthesized a set of 12 receptors constructed with 1,9-diaminoantracene and alpha-amino acid esters, linked via thiourea groups. The association constants and enantioselectivities for the complexes with mandelate and N-acetylphenylalanine were determined by competitive NMR titrations. Association constants quite regularly depend on the substituents in the receptor structure, but the distribution of enantioselectivities across the library could not easily be rationalized.

  DOI：

  10.1021/acs.joc.5b00403
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 在 盐酸 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 L-phenylalanine n-butyl ester hydrochloride
  参考文献：
  名称：

  Chiral Recognition of Carboxylates by a Static Library of Thiourea Receptors with Amino Acid Arms

  摘要：

  Chiral recognition is based on a large network of very subtle interactions whose outcome is difficult to predict. A combinatorial approach is therefore the most suitable to search for the most efficient receptor and obtain a structure-enantioselectivity correlation. We synthesized a set of 12 receptors constructed with 1,9-diaminoantracene and alpha-amino acid esters, linked via thiourea groups. The association constants and enantioselectivities for the complexes with mandelate and N-acetylphenylalanine were determined by competitive NMR titrations. Association constants quite regularly depend on the substituents in the receptor structure, but the distribution of enantioselectivities across the library could not easily be rationalized.

  DOI：

  10.1021/acs.joc.5b00403

文献信息

• Method and compositions for identifying anti-HIV therapeutic compounds
  申请人：GILEAD SCIENCES, INC.

  公开号：US20040121316A1

  公开（公告）日：2004-06-24

  Methods are provided for identifying anti-HIV therapeutic compounds substituted with carboxyl ester or phosphonate ester groups. Libraries of such compounds are screened optionally using the novel enzyme GS-7340 Ester Hydrolase. Compositions and methods relating to GS-7340 Ester Hydrolase also are provided.

  提供了一种鉴定含有羧酸酯或磷酸酯基团抗HIV治疗化合物的方法。可以选择使用新型酶GS-7340酯水解酶筛选这类化合物的文库。还提供了与GS-7340酯水解酶相关的组合物和方法。
• Antimicrobial toxicity studies of ionic liquids leading to a ‘hit’ MRSA selective antibacterial imidazolium salt
  作者：Deborah Coleman、Marcel Špulák、M. Teresa Garcia、Nicholas Gathergood

  DOI：10.1039/c2gc16090k

  日期：——

  Imidazolium salts can be classed as surfactants, detergents, ionic liquids, reagents, catalysts or solvents. A study of the toxicity and ecotoxicity of these salts yields valuable information for their use as pharmaceuticals as well as impact on the environment. Our approach to screen a series of chiral imidazolium salts for toxicity to bacteria and fungi, including clinical pathogen strains, has led to the identification of a ‘hit’ MRSA selective antimicrobial compound. Preliminary structure–activity-relationship (SAR) information (required position of L-phenylalanine and L-valine group) is also elucidated within this first generation of compounds. Conversely, most of the imidazolium salts were nontoxic (IC95 > 2 mM) to the 12 fungi strains and 8 bacteria strains screened, and we propose that they are suitable candidates for ‘green chemistry’ applications. Ecotoxicity studies (Biodegradation ISO 14593 ‘CO2 Headspace Test’) of two bromide ionic liquids containing L-phenylalanine residues indicate that these ionic liquids passed the test (>60% in 28 days) and classed as readily biodegradable.

  咪唑盐可分类为表面活性剂、洗涤剂、离子液体、试剂、催化剂或溶剂。对这些盐的毒性和生态毒性的研究，为其作为药物的使用以及对环境的影响提供了宝贵的信息。我们对一系列手性咪唑盐对细菌和真菌的毒性进行了筛选，包括临床病原菌株，从而鉴定出一种针对MRSA的选择性抗菌化合物。初步的结构-活性关系（SAR）信息（L-苯丙氨酸和L-缬氨酸集团所需的定位）也在这一代化合物中得以阐明。相反，大多数咪唑盐对筛选的12种真菌株和8种细菌株无毒（IC95 > 2 mM），我们提出它们是适合“绿色化学”应用的候选物质。生态毒性研究（ISO 14593生物降解“CO2顶空测试”）表明，含有L-苯丙氨酸残基的两种溴离子液体通过了测试（28天内>60%），被归类为易于生物降解。
• [EN] PHOSPHONATES, MONOPHOSPHONAMIDATES, BISPHOSPHONAMIDATES FOR THE TREATMENT OF VIRAL DISEASES<br/>[FR] PHOSPHONATES, MONOPHOSPHONAMIDATES, BISPHOSPHONAMIDATES POUR TRAITER DES MALADIES VIRALES
  申请人：GILEAD SCIENCES INC

  公开号：WO2005066189A1

  公开（公告）日：2005-07-21

  Compounds and compositions of Formula (I) are described, useful as anti-proliferative agents, and in particular anti-HPV.

  化合物和组合物的化学式（I）被描述，可用作抗增殖剂，特别是抗HPV。
• 核苷酸混合氨基磷酸酯化合物、其药物组合物及其应用
  申请人：佛山科学技术学院

  公开号：CN112300236A

  公开（公告）日：2021-02-02

  本发明属于医药技术领域，公开了核苷酸混合氨基磷酸酯化合物、其药物组合物及其应用，特别是作为治疗新冠肺炎的用途。试验证明本发明化合物具有抑制2019‑nCoV病毒复制的活性，同时所述化合物具有比目前治疗新冠肺炎药物瑞德西韦体外活性高、开发系数大等优点，可用于治疗新冠肺炎药物的开发。
• Synthesis of phosphonate derivatives of 2′-deoxy-2′-fluorotetradialdose d-nucleosides and tetradialdose d-nucleosides
  作者：Tomáš Lášek、Juraj Dobiáš、Miloš Buděšínský、Jaroslav Kozák、Barbora Lapuníková、Ivan Rosenberg、Gabriel Birkuš、Ondřej Páv

  DOI：10.1016/j.tet.2021.132159

  日期：2021.6

  Analogs of nucleosides and nucleotides represent a promising pool of potential therapeutics. This work describes a new synthetic route leading to 2′-deoxy-2′-fluorotetradialdose D-nucleoside phosphonates. Moreover, a new universal synthetic route leading to tetradialdose d-nucleosides bearing purine nucleobases is also described. All new compounds were tested as triphosphate analogs for inhibitory

  核苷和核苷酸的类似物代表了一个有前途的潜在疗法库。这项工作描述了一种新的合成路线，可生成 2'-deoxy-2'-fluorotetradiadose D-nucleoside phosphonates。此外，还描述了一种新的通用合成路线，该路线导致带有嘌呤核碱基的四二醛糖d-核苷。所有新化合物都作为三磷酸盐类似物对多种病毒聚合酶的抑制效力进行了测试。氟化核苷被转化为氨基磷酸酯前药，并在细胞培养物中对包括流感和 SARS-CoV-2 在内的各种病毒进行了评估。