β-alanine | 110762-24-8

• 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: β-alanine
• 英文别名: 3-[2-Phosphonomethylphenyl]-2-aminopropanoic acid；2-(Phosphonomethyl)phenylalanine；2-amino-3-[2-(phosphonomethyl)phenyl]propanoic acid
• CAS: 110762-24-8
• 化学式: C₁₀H₁₄NO₅P
• 分子量: 259.199
• InChiKey: MRGUIJVNFRTRSF-UHFFFAOYSA-N

物化性质

• 熔点：
  238-244 °C (decomp)
• 沸点：
  536.0±60.0 °C(Predicted)
• 密度：
  1.499±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  邻二氯苄 在 盐酸 、 亚磷酸 、 乙醇 作用下， 以 乙醇 为溶剂， 反应 29.25h， 生成 β-alanine
  参考文献：
  名称：

  Phosphorus-containing aminocarboxylic acids with an o-xylylene fragment. III

  摘要：

  DOI：

  10.1007/bf00772025

文献信息

• Evaluation of the amino acid binding site of Mycobacterium tuberculosis glutamine synthetase for drug discovery
  作者：Anneli Nordqvist、Mikael T. Nilsson、Svenja Röttger、Luke R. Odell、Wojciech W. Krajewski、C. Evalena Andersson、Mats Larhed、Sherry L. Mowbray、Anders Karlén

  DOI：10.1016/j.bmc.2008.04.015

  日期：2008.5

  of a literature survey, structure-based virtual screening and synthesis of a small library was performed to identify hits to the potential antimycobacterial drug target, glutamine synthetase. The best inhibitor identified from the literature survey was (2S,5R)-2,6-diamino-5-hydroxyhexanoic acid (4, IC(50) of 610+/-15microM). In the virtual screening 46,400 compounds were docked and subjected to a pharmacophore

  进行文献调查，基于结构的虚拟筛选和小文库合成的组合，以鉴定对潜在的抗分枝杆菌药物靶标谷氨酰胺合成酶的命中。从文献调查中确定的最佳抑制剂是（2S，5R）-2,6-二氨基-5-羟基己酸（4，IC（50）610 +/- 15microM）。在虚拟筛选中，对接了46,400种化合物，并进行了药效团搜索。在这些化合物中，购买了29种并在生物学分析中进行了测试，从而可以鉴定出三种含有芳香族支架的新型抑制剂。基于虚拟筛选的命中结果之一，合成了一个由15个类似物组成的小型文库，产生了四种抑制谷氨酰胺合成酶的化合物。
• Antagonists of specific excitatory amino acid neurotransmitter receptors
  申请人：NOVA PHARMACEUTICAL CORPORATION

  公开号：EP0242709A2

  公开（公告）日：1987-10-28

  The invention pertains to novel, potent anticonvulsants, analgesics and cognition enhancers achieving their action through the antagonism of specific excitatory amino acid neurotransmitter receptors. In particular, the invention is directed to ω-[2-phosphonoalkylenyl)phenyl]-2-­aminoalkanoic acids having general formula: Wherein R₁ and R₂ are the same or different and are selected from the group consisting of hydrogen, lower alkyl, halogen, -CH=CH-CH=CH=, amino, nitro, trifluoromethyl or cyano; n and m = 0, 1, 2 or 3; and the pharmaceutically acceptable salts and derivatives thereof. Examples of specific preferred compounds of general formula are selected from the group consisting of: 4-[2-­phosphonomethylphenyl]-2-aminobutanoic acid, ethyl 3-[2-(2-­ (2-diethylphosphonoethyl)phenyl]-2-acetamido-2-­carboethoxypropanoate, 3-[2-phosphonomethyl)phenyl]-2-­aminopropanoic acid, ethyl 3-[2-(3-bromopropyl)phenyl]-2-­acetamido-3-carboethoxypropanoate, ethyl 3-[2-(3-­diethylphosphonopropyl)phenyl]-2-acetamido-2-­carboethoxypropanoate, ethyl 3-[2-(3-phosphonopropyl)-­phenyl]-2-aminopropanoic acid, ethyl 5-[2-­(diethylphosphonomethyl)-phenyl]-2- acetamido-2-­carboethoxypentanoate, and 5-[2-phosphonomethylphenyl]-2-­aminopentanoic acid. Furthermore, the invention relates to a process for preparing the said potent, selective excitatory amino acid neurotransmitter receptor antagonist.

  本发明涉及通过拮抗特定兴奋性氨基酸神经递质受体而发挥作用的新型强效抗惊厥药、镇痛药和认知增强剂。本发明尤其涉及通式为ω-[2-膦酰基烷烯基]苯基]-2-氨基烷酸： 其中，R₁ 和 R₂ 相同或不同，且选自由氢、低级烷基、卤素、-CH=CH-CH=CH=、氨基、硝基、三氟甲基或氰基组成的组；n 和 m = 0、1、2 或 3；及其药学上可接受的盐和衍生物。 具体优选的通式化合物的例子选自以下组成的组：4-[2-膦酰甲基苯基]-2-氨基丁酸、3-[2-(2-二乙基膦酰乙基)苯基]-2-乙酰氨基-2-羧乙氧基丙酸乙酯、3-[2-膦酰甲基)苯基]-2-氨基丙酸、3-[2-(3-溴丙基)苯基]-2-乙酰氨基-3-羧乙氧基丙酸乙酯、3-[2-(3-二乙基膦丙基)苯基]-2-乙酰氨基-2-羧乙氧基丙酸乙酯、3-[2-(3-膦丙基)-苯基]-2-氨基丙酸乙酯、5-[2-(二乙基膦甲基)-苯基]-2-乙酰氨基-2-羧乙氧基戊酸乙酯和 5-[2-膦甲基苯基]-2-氨基戊酸乙酯。此外，本发明还涉及一种制备上述强效、选择性兴奋性氨基酸神经递质受体拮抗剂的工艺。
• Phenyl glycines for use in reducing neurotoxic injury
  申请人：G.D. Searle & Co.

  公开号：EP0313002A2

  公开（公告）日：1989-04-26

  A class of phenyl glycine compounds is described for treatment to reduce neurotoxic injury associated with anoxia or ischemia which typically follows stroke, cardiac arrest or perinatal asphyxia. The treatment includes administration of a phenyl glycine compound alone or in a composition in an amount effective as an antagonist to inhibit excitotoxic actions at major neuronal excitatory amino acid receptor sites.

  描述了一类苯基甘氨酸化合物，用于治疗减少与缺氧或缺血有关的神经毒性损伤，缺氧或缺血通常发生在中风、心脏骤停或围产期窒息之后。治疗方法包括单独施用或在组合物中施用苯基甘氨酸化合物，施用量应能有效抑制主要神经元兴奋性氨基酸受体部位的兴奋毒性作用。
• Phosphono-hydroisoquinoline compounds useful in reducing neurotoxic injury
  申请人：G.D. Searle & Co.

  公开号：EP0364996A2

  公开（公告）日：1990-04-25

  A class of phosphono-hydroisoquinoline compounds is described for treatment to reduce neurotoxic injury associated with anoxia or ischemia which typically follows stroke, cardiac arrest or perinatal asphyxia. The treatment includes administration of a phosphono-hydroisoquinoline compound alone or in a composition in an amount effective as an antagonist to inhibit excitotoxic actions at major neuronal excitatory amino acid receptor sites. Compounds of most interest are those of Formula 1: wherein each of R' through R4 is hydrido, wherein each of Z1 and Z2 is hydroxyl, wherein W is a single bond connecting the phosphorus atom with the aromatic ring and wherein the A ring is aromatic. Also disclosed are two classes of intermediate compounds having a fully unsaturated A ring, which intermediate compounds are useful in methods to make product compounds of Formula I.

  描述了一类膦酰基氢化异喹啉化合物，用于治疗减少与缺氧或缺血相关的神经毒性损伤，缺氧或缺血通常发生在中风、心脏骤停或围产期窒息之后。治疗方法包括单独施用或在组合物中施用膦酰基氢化异喹啉化合物，施用量应能有效地作为拮抗剂抑制主要神经元兴奋性氨基酸受体部位的兴奋毒性作用。最令人感兴趣的化合物是式 1： 其中，R'到 R4 中的每一个都是氢基，Z1 和 Z2 中的每一个都是羟基，W 是连接磷原子和芳香环的单键，A 环是芳香环。还公开了两类具有完全不饱和 A 环的中间体化合物，这些中间体化合物在制造式 I 产品化合物的方法中是有用的。
• Imidazo[1,2-a]pyridinylalkyl compounds for treatment of neurotoxic injury
  申请人：G.D. Searle & Co.

  公开号：EP0436831A2

  公开（公告）日：1991-07-17

  A class of imidazo[1,2-a]pyridinylalkyl compounds is described for treatment to reduce neurotoxic injury associated with anoxia or ischemia which typically follows stroke, cardiac arrest or perinatal asphyxia. The treatment includes administration of a compound of this class alone or in a composition in an amount effective as an antagonist to inhibit excitotoxic actions at major neuronal excitatory amino acid receptor sites. Compounds of most interest are those of the formula: wherein each of R22, R23 and R24 is independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl; wherein each of Ym and Yn is a spacer group independently selected methylene and ethylene radicals which may be unsubstituted and from methylene radicals which may be substituted with a group selected from halo, hydroxy and oxo; wherein each of m and n is a number independently selected from zero to two, inclusive; wherein each X and T is one or more groups independently selected from hydrido, alkyl, cycloalkyl, halo, haloalkyl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl and alkanoyl; or a pharmaceutically-acceptable salt thereof.

  描述了一类咪唑并[1,2-a]吡啶烷基化合物，用于治疗减少与缺氧或缺血相关的神经毒性损伤，这种损伤通常发生在中风、心脏骤停或围产期窒息之后。治疗方法包括单独施用或在组合物中施用该类化合物，施用量为有效的拮抗剂，以抑制主要神经元兴奋性氨基酸受体部位的兴奋毒性作用。最令人感兴趣的化合物是式中的化合物： 其中 R22、R23 和 R24 各自独立地选自肼、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、环丙基、环丁基、环戊基、环己基和环庚基；其中 Ym 和 Yn 各自是一个间隔基团，该间隔基团独立地选自可能未被取代的亚甲基和亚乙基，以及可能被选自卤代、羟基和氧代的基团取代的亚甲基；其中每个 m 和 n 是独立选自 0 至 2（包括 2）的数字；其中每个 X 和 T 是一个或多个独立选自氢基、烷基、环烷基、卤基、卤代烷基、羟基、羟基烷基、烷氧基、烷氧基烷基和烷酰基的基团；或其药学上可接受的盐。