<1-(alanylamino)ethyl>phosphonic acid | 423124-71-4

• 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: <1-(alanylamino)ethyl>phosphonic acid
• 英文别名: 1-(L-Alanylamino)-ethanephosphonic acid；1-(N-L-alanylamino)ethanephosphonicacid；N-L-alanyl-1-aminoethylphosphonic acid；N-alanyl-1-aminoethanephophonic acid；alafosfalin；1R-(L-alanylamino)-ethanephosphonic acid；1-[[(2S)-2-aminopropanoyl]amino]ethylphosphonic acid
• CAS: 423124-71-4
• 化学式: C₅H₁₃N₂O₄P
• 分子量: 196.143
• InChiKey: BHAYDBSYOBONRV-WUCPZUCCSA-N

物化性质

• 密度：
  1.395±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  <1-(alanylamino)ethyl>phosphonic acid 生成 阿拉磷 、 N-(S)-alanyl-(S)-1-aminoethanephosphonic acid
  参考文献：
  名称：

  Phosphonodipeptides: synthesis and separation of diastereoisomers

  摘要：

  磷酰二肽的不对映异构体混合物，是由来自外消旋二烷基1-氨基烷基膦酸酯的制备而成的，通过离子交换柱色谱法进行分离。发现从二烷基1-氨基烷基膦酸酯中更容易得到磷酰二肽，而不是从相应的游离酸中获得，混合羧酸-碳酸酐法被发现是最有效的方法。

  DOI：

  10.1139/v82-441
• 作为产物：
  描述：

  (2S)-2-amino-N-(1-diphenoxyphosphorylethyl)propanamide 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 <1-(alanylamino)ethyl>phosphonic acid
  参考文献：
  名称：

  Transesterification of Diphenyl Phosphonates using the Potassium Fluoride/Crown Ether/Alcohol System; Part 2. The Use of Diphenyl 1-Aminoalkanephosphonates in Phosphonopeptide Synthesis

  摘要：

  DOI：

  10.1055/s-1982-29818

文献信息

• Conversion of amino acids and dipeptides into their phosphonic analogs
  作者：George Ösapay、Ildikó Szilagyi、Jenö Seres

  DOI：10.1016/s0040-4020(01)86836-8

  日期：1987.1

  Acylamino carboxylic acids were degradated by the Hunsdiecker-reaction; the bromo-derivatives were reacted with NaPO(OC2H5)2. Aminophosphonic acids were obtained by acidic hydrolysis, and half-blocked derivatives by the selective removal of masking substituents. Two phosphonopeptides [e.g. Alafosfalin (4i)] were also prepared by this route.

  酰基氨基羧酸通过Hunsdiecker反应被降解。溴衍生物与NaPO（OC 2 H 5）2反应。通过酸性水解获得氨基膦酸，通过选择性去除掩蔽取代基获得半封闭的衍生物。通过该途径也制备了两个磷酸肽[例如Alafosfalin（4i）]。
• Acyl derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04250085A1

  公开（公告）日：1981-02-10

  Peptide derivatives provided by the present invention are compounds of the general formula ##STR1## wherein R.sup.1 represents a hydrogen atom or the methyl or hydroxymethyl group or a mono-, di- or trihalomethyl mgroup; R.sup.2 represents the characterizing group of an .alpha.-amino acid of the type normally found in proteins or a lower alkyl or hydroxy- (lower alkyl) group other than the characterising group of an .alpha.-amino acid of the type normally found in proteins; R.sup.3 represents a lower alkyl, lower cycloalkyl, lower alkenyl, aryl or aryl-(lower alkyl) group; R.sup.4 represents a hydrogen atom or a lower alkyl group; n stands for 1,2 or 3; the configuration at the carbon atom designated as (a) is (R) when R.sup.1 represents other than a hydrogen atom and the configuration at the carbon atom designated as (b) is (L) when R.sup.2 represents other than a hydrogen atom, and pharmaceutically acceptable salts thereof. The compounds exhibit activity as antibacterial agents against a range of gram-positive and gram-negative bacteria. Also disclosed are intermediates and a process for the production of the end product.

  本发明提供的肽衍生物是具有一般式##STR1##的化合物，其中R.sup.1代表氢原子或甲基或羟甲基基团或单、二或三卤甲基基团；R.sup.2代表通常在蛋白质中发现的α-氨基酸的特征基团或低烷基或除了通常在蛋白质中发现的α-氨基酸的特征基团以外的羟基-(低烷基)基团；R.sup.3代表低烷基、低环烷基、低烯基、芳基或芳基-(低烷基)基团；R.sup.4代表氢原子或低烷基基团；n代表1、2或3；当R.sup.1代表除氢原子以外的其他基团时，指定为(a)的碳原子处的构型为(R)，当R.sup.2代表除氢原子以外的其他基团时，指定为(b)的碳原子处的构型为(L)，以及其药学上可接受的盐。这些化合物表现出抗一系列革兰氏阳性和革兰氏阴性细菌的活性。还披露了中间体和生产终产品的方法。
• Chemical process for the production of .alpha.-aminophosphonic acids and
  申请人：Ciba-Geigy Corporation

  公开号：US04331591A1

  公开（公告）日：1982-05-25

  The present invention provides a process for the production of physiologically-useful .alpha.-aminophosphonic acids and peptide derivatives of the formula: ##STR1## wherein R and R.sub.1 may be the same or different and each can be hydrogen, deuterium or an optionally substituted lower alkyl group, lower alkenyl, lower alkynyl, cycloalkyl, aryl or heterocyclic radical containing one or more oxygen, nitrogen or sulphur atoms and which may be fused to an aromatic ring, a lower alkyl group substituted by a cycloalkyl radical, a lower alkyl group substituted by an aryl radical, a lower alkyl group substituted by a heterocyclic radical as defined above or R and R.sub.1 together form a polymethylene chain optionally interrupted by an oxygen, nitrogen or sulphur atom, or R.sub.1 represents, together with the C(R)--N< residue to which it is attached, the atoms required to complete a heterocyclic radical; and R.sub.2 can be hydrogen, optionally substituted lower alkyl, cycloalkyl, aryl or lower alkyl substituted by a cycloalkyl radical, lower alkyl substituted by a heterocyclic radical containing one or more nitrogen atoms; by a heterocyclic radical containing one or more nitrogen atoms, or R.sub.2 together with the C(H)--N residue to which it is attached, may represent the atoms required to complete a heterocyclic radical; and n is 0, 1, 2, 3 or 4; comprising oxidizing, using an oxidizing agent, a compound having the formula: ##STR2## wherein R, R.sup.1, R.sup.2 and n have their previous significance, and Z is H or a protecting group usually used for an amino group; and then removing any protecting group.

  本发明提供了一种制备生理有用的α-氨基膦酸和肽衍生物的方法，其化学式为：##STR1## 其中R和R.sub.1可以相同也可以不同，每个可以是氢、氘或者是一个含有一个或多个氧、氮或硫原子的可选取代的较低烷基、较低烯基、较低炔基、环烷基、芳基或杂环基，并且可以与芳香环融合，可以是一个由环烷基取代的较低烷基，可以是一个由芳基取代的较低烷基，可以是一个由上述定义的杂环基取代的较低烷基，或者R和R.sub.1一起形成一个可以由氧、氮或硫原子中断的聚甲基链，或者R.sub.1表示与其连接的C(R)--N<残基一起，需要完成一个杂环基的原子；R.sub.2可以是氢、可选取代的较低烷基、环烷基、芳基或者由环烷基取代的较低烷基、由含有一个或多个氮原子的杂环基取代的较低烷基，或者是由含有一个或多个氮原子的杂环基取代的较低烷基，或者R.sub.2与其连接的C(H)--N残基一起，可以表示需要完成一个杂环基的原子；n为0、1、2、3或4。该方法包括使用氧化剂氧化化合物，该化合物的化学式为：##STR2## 其中R、R.sup.1、R.sup.2和n具有其前述的意义，Z为H或通常用于氨基的保护基；然后去除任何保护基。
• Amino acids and peptides. V. Synthesis of N-L- and D- alanyl-1-aminoethylphosphonic acids.
  作者：YOSHIO OKADA、SHIN IGUCHI、MASASHI MIMURA、MASAMI YAGYU

  DOI：10.1248/cpb.28.1320

  日期：——

  N-L-Alanyl-1-aminoethylphosphonic acid (IIIa) and N-D-alanyl-1-aminoethylphos-phonic acid (IIIb) were synthesized. IIIb did not exhibit any antibacterial activity against gram-positive or gram-negative organisms, but IIIa showed antibacterial activity against some gram-negative organisms.

  合成了 N-L-丙氨酰-1-氨乙基膦酸（IIIa）和 N-D-丙氨酰-1-氨乙基膦酸（IIIb）。IIIb 对革兰氏阳性或革兰氏阴性菌均无抗菌活性，但 IIIa 对某些革兰氏阴性菌具有抗菌活性。
• Kametani, Tetsuji; Kigasawa, Kazuo; Hiiragi, Mineharu, Heterocycles, 1981, vol. 16, # 7, p. 1205 - 1242
  作者：Kametani, Tetsuji、Kigasawa, Kazuo、Hiiragi, Mineharu、Wakisaka, Kikuo、Haga, Seiji、et al.

  DOI：——

  日期：——