4-(2-CARBOXY-ETHYL)-5-OXO-OXAZOLIDINE-3-CARBOXYLIC ACID BENZYL ESTER | 19525-56-5

• 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: 4-(2-CARBOXY-ETHYL)-5-OXO-OXAZOLIDINE-3-CARBOXYLIC ACID BENZYL ESTER
• 英文别名: 3-{3-[(benzyloxy)carbonyl]-5-oxo-1,3-oxazolidin-4-yl}propanoic acid；3-benzyloxycarbonyl-4-(2-hydroxycarbonylethyl)oxazolidin-5-one；(4S)-4-(2-Carboxyethyl)-3-[(phenylmethoxy)carbonyl]oxazolidin5-one；DL-3-benzyloxycarbonyl-4-(2-carboxyethyl)oxazolidin-5-one；N-carbobenzoxy-4-(β-carboxyethyl)-oxazolidin-5-one；3-(5-oxo-3-phenylmethoxycarbonyl-1,3-oxazolidin-4-yl)propanoic acid
• CAS: 19525-56-5
• 化学式: C₁₄H₁₅NO₆
• mdl: MFCD06660665
• 分子量: 293.276
• InChiKey: AYOCGDFDOZVEKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2-CARBOXY-ETHYL)-5-OXO-OXAZOLIDINE-3-CARBOXYLIC ACID BENZYL ESTER 在 palladium on activated charcoal 三乙基硅烷 、 氢气 、 三氟乙酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 120.0h， 生成 N-甲基-DL-谷氨酸
  参考文献：
  名称：

  Synthesis and Structural Characterization of N-Methyl-DL-glutamic Acid

  摘要：

  通过单晶X射线衍射技术，定义了混合的N-甲基谷氨酸的固态构象。正交晶体属于空间群Pbca，a为15.219(2) Å，b为10.583(1) Å，c为9.595(1) Å，Z为8。该结构被精细地修正到最终的R值为0.049，共测量了1285个数据。在晶体中，分子采用带电离子形式，氨基氮原子发生了质子化。α-羧基未质子化，而d-羧基保留了质子。红外光谱表明，氨基酸处于带电离子形式。晶体中的分子通过羧酸质子和N原子上的两个质子之间的分子间氢键连接成三维网络。

  DOI：

  10.1071/ch99182
• 作为产物：
  描述：

  N-苄氧羰基-L-谷氨酸 在 silica gel 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 4-(2-CARBOXY-ETHYL)-5-OXO-OXAZOLIDINE-3-CARBOXYLIC ACID BENZYL ESTER
  参考文献：
  名称：

  Beta-strand mimetics and method relating thereto

  摘要：

  本发明揭示了在生物活性肽和蛋白质的β-链区域中模拟二级结构的构象约束化合物。这种β-链模拟结构在广泛的领域中具有实用性，包括作为诊断和治疗剂。本发明还揭示了含有这种β-链模拟结构的文库，以及筛选这些结构以识别具有生物活性的成员的方法。

  公开号：

  US20040053331A1

文献信息

• The Facile Production of N-Methyl Amino Acids via Oxazolidinones
  作者：Luigi Aurelio、Robert T. C. Brownlee、Andrew B. Hughes、Brad E. Sleebs

  DOI：10.1071/ch99082

  日期：——

  A range of oxazolidinones derived from N-carbamoylα-amino acids were prepared by an efficient method as key intermediatesin the synthesis of N-methyl amino acids and peptides.The method was readily applied to most α-amino acids except those withbasic side chains. The oxazolidinones were converted by reductive cleavageinto N-methyl α-amino acids.

  以N-氨基甲酰基α-氨基酸为原料，制备了一系列恶唑烷酮类化合物，作为合成N-甲基氨基酸和多肽的关键中间体。该方法适用于除碱性侧链以外的大多数α-氨基酸。恶唑烷酮通过还原裂解转化为N-甲基α-氨基酸。
• N-acyl acidic amino acid diamide derivative, a salt thereof, and an
  申请人：Toyama Chemical Co., Ltd.

  公开号：US04610983A1

  公开（公告）日：1986-09-09

  This invention relates to a novel N-acyl acidic amino acid diamide derivative represented by the general formula or a salt thereof: ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, represents a hydrogen atom or a substituted or unsubstituted alkyl, cycloalkyl, alkenyl or aralkyl group, or R.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4, when taken together with the respective adjacent nitrogen atoms, form a substituted or unsubstituted heterocyclic group; R.sup.5 represents a substituted or unsubstituted cycloalkyl, acyl or heterocyclic group; A represents a bond or a substituted or unsubstituted alkylene, alkenylene or alkadienylene group; and n is 1, 2 or 3. Said compound has an anti-ulcer activity which is effective to human beings and animals. This disclosure relates to such a compound, to a process for the production thereof and to an anti-ulcer agent containing the same.

  本发明涉及一种由通式表示的新型N-酰基酸性氨基酸二酰胺衍生物或其盐：其中R.sup.1、R.sup.2、R.sup.3和R.sup.4中的每一个，可以相同也可以不同，代表氢原子或取代或未取代的烷基、环烷基、烯基或芳基，或R.sup.1和R.sup.2和/或R.sup.3和R.sup.4，与相邻的氮原子结合在一起形成取代或未取代的杂环基；R.sup.5代表取代或未取代的环烷基、酰基或杂环基；A代表键或取代或未取代的烷基、烯基或烷二烯基；n为1、2或3。该化合物具有对人类和动物有效的抗溃疡活性。本公开涉及这种化合物，其生产方法以及含有该化合物的抗溃疡剂。
• [EN] BETA-STRAND MIMETICS AND METHOD RELATING THERETO<br/>[FR] STRUCTURES MIMETIQUES DE BRIN BETA ET PROCEDE ASSOCIE
  申请人：CHOONGWAE PHARMA CORP

  公开号：WO2004108731A1

  公开（公告）日：2004-12-16

  Conformationally constrained compounds which mimic the secondary structure of ß-strand regions of biologically active peptides and proteins are disclosed. Such ß-strand mimetic structures have utility over a wide range of fields, including use as diagnostic and therapeutic agents. Libraries containing the ß-strand mimetic structures of this invention are also disclosed as well as methods for screening the same to identify biologically active members.

  披露了在生物活性肽和蛋白质的β-折叠区域模拟次级结构的构象受限化合物。这种β-链模拟结构在广泛领域内具有实用价值，包括用作诊断和治疗药物。还披露了含有本发明的β-链模拟结构的文库，以及筛选这些结构以识别生物活性成员的方法。
• Reductive radical decarboxylation of amino-acids and peptides
  作者：Derek H. R. Barton、Yolande Hervé、Pierre Potier、Josiane Thierry

  DOI：10.1039/c39840001298

  日期：——

  Radicals generated from N-protected α-amino-acids by photolysis of their N-hydroxypyridine-2-thione esters at room temperature are efficiently quenched by t-butyl thiol to give decarboxy-acids; comparable reactions have been carried out on the side chain carboxy groups of suitably protected aspartic and glutamic acids.

  由N-保护的α-氨基酸在室温下光解其N-羟基吡啶-2-硫酮酯所产生的自由基被叔丁基硫醇有效地淬灭，得到脱羧酸；在适当保护的天冬氨酸和谷氨酸的侧链羧基上已经进行了类似的反应。
• Nonapeptide and decapeptide analogs of LHRH useful as LHRH antagonists, their preparation and compositions containing them
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0097031A2

  公开（公告）日：1983-12-28

  Nonapeptide and decapeptide analogs of LHRH which have the formula and the pharmaceutically acceptable salts thereof, wherein: A is an amino acyl residue selected from the group consisting of L-pyroglutamyl, D-pyroglutamyl, N-acyl-D,L-tryptophanyl, N-acyl-glycyl, N-Ac-D,L-Δ3,4-prolyl, N-Ac-D,L-prolyl, N-Ac-L-alkylprolyl, N-Ac-D,L-phenylalanyl, N-Ac-D,L-p-chlorophenylalanyl, N-Ac-D,L-seryl, N-Ac-D,L-threonyl, N-Ac-D,L-alanyl, 3-(1-naphthyl)-D,L-alanyl, 3-(2-naphthyl)-D,L-alanyl, 3-(2,4,6-trimethylphenyl)-D,L-alanyl, 3-(4-trifluoromethylphenyl)-D,L-alanyl, 3-(9-anthryl)-D,L-alanyl, 3-(2-fluorenyl)-D,L-alanyl, and 3-(Het)-D,L-alanyl wherein Het is a heterocyclic aryl containing radical selected from wherein A" and A' are independently selected from the group consisting of hydrogen, lower alkyl, chlorine and bromine, and G is selected from the group consisting of oxygen, nitrogen and sulfur; B is an amino acyl residue selected from the group consisting of D-phenylalanyl, D-p-Cl-phenylalanyl, D-p-F-phenylalanyl, D-p-nitrophenylalanyl, 3-(3,4,5-trimethoxyphenyl)-D-alanyl, 2,2-diphenylglycine, D-a-methyl-p-Cl-phenylalanine and 3-(2,4,6-trimethylphenyl)-D-alanyl; C is an amino acyl residue selected from the group consisting of L-tryptophanyl, D-tryptophanyl, D-phenylalanyl, D-Mesphenylalanyl, 3-(2-pyridyl)-D-alanyl, 3-(3-pyridyl)D-alanyl, 3-(1-naphthyl)-D-alanyl, 3-(2-naphthyl)-D-alanyl and 3-(4-pyridyl)-D-alanyl. D is an amino acyl residue selected from the group consisting of L-seryl, and D-alanyl; E is an amino acyl residue selected from the group consisting of L-phenylalanyl and L-tyrosyl; F is an amino acyl selected from the group consisting of the radicals represented by the following structural formulas: wherein n is 1 to 5 ; R, is alkyl of 1 to 12 carbon atoms, -NRR3 wherein R is hydrogen or alkyl of 1 to 4 carbon atoms, R3 is alkyl of 1 to 12 carbon atoms, cycloalkyl, phenyl, benzyl, -(CH2)n-morpholino or -(CH2)nN(R4)2 wherein n is 1 to 5 and R4 is lower alkyl; R2 is hydrogen or R3; or R, and R2 comprise a ring represented by the following structural formulas: wherein n is 1 to 7; A is hydrogen, alkyl of 1 to 6 carbon atoms or cycloalkyl; and X is halo or A or b) H2N-CH-CO2H wherein R5 is alkyl of 1 to 6 carbon atoms, benzyl, phenylethyl, cyclohexyl, cyclopentyl; and R6, R7 and R8 are hydrogen or alkyl of 1 to 4 carbon atoms; and n is the integer 2-5; or C) a substituent of the formula wherein R9 is hydrogen, alkyl of 1 to 12 carbon atoms, phenyl or phenylloweralkyl; G is an amino acyl residue selected from the group consisting of L-leucyl, L-norleucyl and L-norvatyl; H is D-alaninamide, D-leucinamide, glycinamide or -NHR5 wherein R5 is lower alkyl, cycloalkyl, fluoro lower alkyl, or NHCONH-R10 wherein R,o is hydrogen or lower alkyl; and the pharmaceutically acceptables salts thereof.

  LHRH 的非肽和十肽类似物，其分子式为 及其药学上可接受的盐类，其中 A 是一个氨基酰基残基，选自由 L-焦谷氨酰、D-焦谷氨酰、N-酰基-D,L-色氨酰、N-酰基-甘氨酰、N-Ac-D、L-Δ3,4-脯氨酰，N-Ac-D,L-脯氨酰，N-Ac-L-烷基脯氨酰，N-Ac-D,L-苯丙氨酰，N-Ac-D,L-氯苯丙氨酰，N-Ac-D,L-丝氨酰，N-Ac-D,L-苏氨酰、N-Ac-D,L-丙氨酰，3-(1-萘基)-D,L-丙氨酰，3-(2-萘基)-D,L-丙氨酰，3-(2,4,6-三甲基苯基)-D,L-丙氨酰，3-(4-三氟甲基苯基)-D,L-丙氨酰、3-(9-蒽基)-D,L-丙氨酰、3-(2-芴基)-D,L-丙氨酰和 3-(Het)-D,L-丙氨酰，其中 Het 是选自以下的含杂环芳基的基团 其中 A "和 A'独立地选自氢、低级烷基、氯和溴组成的组，G 选自氧、氮和硫组成的组； B 是氨基酰基残基，选自由 D-苯丙氨酰、D-对氯苯丙氨酰、D-对 F-苯丙氨酰、D-对硝基苯丙氨酰、3-(3,4,5-三甲氧基苯基)-D-丙氨酰、2,2-二苯基甘氨酸、D-a-甲基对氯苯丙氨酰和 3-(2,4,6-三甲基苯基)-D-丙氨酰组成的组； C 是氨基酰基残基，选自由 L-色氨酰、D-色氨酰、D-苯丙氨酰、D-甲苯丙氨酰、3-(2-吡啶基)-D-丙氨酰、3-(3-吡啶基)-D-丙氨酰、3-(1-萘基)-D-丙氨酰、3-(2-萘基)-D-丙氨酰和 3-(4-吡啶基)-D-丙氨酰组成的组。 D 是选自 L-丝氨酰和 D-丙氨酰的氨基酰基残基； E 是一个氨基酰基残基，选自由 L-苯丙氨酰和 L-酪氨酰组成的组； F 是一个氨基酰基，选自由下列结构式所代表的基团组成的组： 其中 n 为 1 至 5； R，是 1 至 12 个碳原子的烷基，-NRR3，其中 R 是氢或 1 至 4 个碳原子的烷基，R3 是 1 至 12 个碳原子的烷基、环烷基、苯基、苄基、-(CH2)n-吗啉基或-(CH2)nN(R4)2，其中 n 是 1 至 5，R4 是低级烷基； R2 是氢或 R3；或 R 和 R2 由以下结构式代表的环组成： 其中 n 为 1 至 7；A 为氢、1 至 6 个碳原子的烷基或环烷基；X 为卤素或 A 或 b) H2N-CH-CO2H 其中 R5 是 1 至 6 个碳原子的烷基、苄基、苯乙基、环己基、环戊基；R6、R7 和 R8 是氢或 1 至 4 个碳原子的烷基；n 是 2 至 5 的整数；或 C) 式中的取代基 其中 R9 是氢、1 至 12 个碳原子的烷基、苯基或苯基低级烷基； G 是选自 L-亮氨酰，L-正亮氨酰和 L-正藜芦酰的氨基酰基残基； H 是 D-丙氨酰胺、D-亮氨酰胺、甘氨酰胺或-NHR5，其中 R5 是低级烷基、环烷基、氟低级烷基或 NHCONH-R10，其中 R,o 是氢或低级烷基；及其药学上可接受的盐。