苄氧羰基-beta-丙氨酸对硝基苯酯 | 3642-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 苄氧羰基-beta-丙氨酸对硝基苯酯
• 英文名称: N-carbobenzoxy-β-alanine-p-nitrophenyl ester
• 英文别名: benzyloxycarbonyl-β-alanine p-nitrophenyl ester；4-nitrophenyl benzyloxycarbonyl-β-alanine；3-<(benzyloxycarbonyl)amino>propionic acid 4-nitrophenyl ester；p-nitrophenyl ester of N-benzyloxycarbonyl-β-alanine；N-β-Carbobenzoxyalanine p-nitrophenyl ester；p-nitrophenyl ester of N-(benzyloxycarbonyl)-3-aminopropionic acid；N-Benzyloxycarbonyl-β-alanin-(4-nitro-phenylester)；N-benzyloxycarbonyl β-alanine p-nitrophenyl ester；N-Benzyloxycarbonyl-β-alanin-p-nitrophenylester；carbobenzoxy-β-alanine p-nitrophenyl ester；(4-Nitrophenyl) 3-(phenylmethoxycarbonylamino)propanoate
• CAS: 3642-91-9
• 化学式: C₁₇H₁₆N₂O₆
• 分子量: 344.324
• InChiKey: ZVWBGQBOHVVMEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  苄氧羰基-beta-丙氨酸对硝基苯酯 在 氢溴酸 、 溶剂黄146 作用下， 生成 β-Ala-OPNP
  参考文献：
  名称：

  Matsui,T.; Koga,K., Chemical and pharmaceutical bulletin, 1979, vol. 27, p. 2295 - 2303

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯酚 、 N-CBZ-beta-丙氨酸 在 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 生成 苄氧羰基-beta-丙氨酸对硝基苯酯
  参考文献：
  名称：

  合成含有β-丙氨酸的缓激肽类似物。

  摘要：

  介绍了 6-β-丙氨酸、4-β-丙氨酸和 4，6-二-β-丙氨酸缓激肽的合成。比较了三种类似物与缓激肽的生物活性。

  DOI：

  10.1248/cpb.14.1017

文献信息

• Design and synthesis of a series of combined vasodilator-.beta.-adrenoceptor antagonists based on 6-arylpyridazinones
  作者：R. A. Slater、W. Howson、G. T. G. Swayne、E. M. Taylor、D. R. Reavill

  DOI：10.1021/jm00397a013

  日期：1988.2

  synthesized and evaluated as combined vasodilator/beta-adrenoceptor antagonists and potential antihypertensive agents. Many of the early compounds displayed an unacceptably high level of intrinsic sympathomimetic activity (ISA) and a relatively short duration of action. Disubstitution in the 2,3-positions or in the 4-position of the aryloxy ring gave compounds with low ISA levels and, in some instances,

  已经合成了一系列新的6- [4-[[（（芳氧基）酰基]氨基]苯基] -4,5-二氢吡啶并酮，并被评估为血管扩张剂/β-肾上腺素能受体拮抗剂和潜在的降压药。许多早期化合物显示出高水平的固有拟交感神经活性（ISA）和相对较短的作用时间。在芳氧基环的2，3-位或4-位二取代得到的化合物具有较低的ISA水平，并且在某些情况下改善了作用时间。所有这些化合物都是血管扩张药，但5-甲基哒嗪酮衍生物的抗高血压活性始终高于其5-H较低的同系物。
• Synthesis, characterization, and enzymic conversion of nonhydrolysable analogues of propionylcoenzyme A
  作者：Yimin Zhao、Martina Michenfelder、János Rétey

  DOI：10.1139/v94-025

  日期：1994.1.1

  We describe the synthesis of three novel analogues of propionyl-coenzyme A, in which the sulfur atom has been replaced by methylene, ethylene, and thiomethylene, respectively. All three analogues, propionyl-dethia(carba)-CoA (1), propionyl-dethia(dicarba)-CoA (2), and S-(2-oxobutanyl)-CoA (3) were characterized by ¹H and ³¹P NMR spectroscopy and FAB mass spectrometry. Propionyl-CoA–oxaloacetate transcarboxylase from Propionibacterium shermanii accepted the novel analogues as substrates and carboxylated them to the corresponding methylmalonyl-CoA analogues (4–6). The latter were further converted into the succinyl-CoA analogues by the coenzyme-B₁₂-dependent methylmalonyl-CoA mutase from the same organism. The succinyl-CoA analogues, succinyl-dethia(carba)-CoA (7), succinyl-dethia(dicarba)-CoA (8), and 4-carboxy(2-oxobutanyl)-CoA (9) were obtained on a preparative scale and their Michaelis constants (K_m) with methylmalonyl-CoA mutase were determined to be 0.136, 2.20, and 0.132 mM, respectively (K_m for succinyl-CoA is 0.025 mM). The V_max values for 7, 8, and 9 are 1.1, 0.013, and 0.0047 µmol min⁻¹ U⁻¹, respectively (V_max for succinyl CoA is 1.0). The utility of the novel coenzyme A analogues in enzyme mechanistic studies is discussed.

  我们描述了三种新的丙酰辅酶A类似物的合成，其中硫原子分别被亚甲基、乙烯基和硫亚甲基取代。这三种类似物，丙酰-去硫（碳）-辅酶A（1）、丙酰-去硫（二碳）-辅酶A（2）和S-(2-氧丁酰)-辅酶A（3）通过¹H和³¹P核磁共振光谱和FAB质谱进行了表征。来自谢尔曼丙酸杆菌的丙酰辅酶A-草酰乙酸转羧酶接受了这些新的类似物作为底物，并将它们羧化为相应的甲基丙二酰辅酶A类似物（4-6）。后者进一步由同一生物体内的辅酶B₁₂依赖的甲基丙二酰辅酶A异构酶转化为琥珀酰辅酶A类似物。在制备规模上获得了琥珀酰-去硫（碳）-辅酶A（7）、琥珀酰-去硫（二碳）-辅酶A（8）和4-羧基(2-氧丁酰)-辅酶A（9），并确定了它们与甲基丙二酰辅酶A异构酶的米氏常数（K_m)分别为0.136、2.20和0.132 mM（琥珀酰辅酶A的K_m为0.025 mM）。7、8和9的V_max值分别为1.1、0.013和0.0047 µmol min⁻¹ U⁻¹（琥珀酰辅酶A的V_max为1.0）。讨论了新型辅酶A类似物在酶机理研究中的实用性。
• Synthesis of ω-amino acid peptides related to leucine-enkephalin
  作者：FHC Stewart

  DOI：10.1071/ch9812439

  日期：——

  Syntheses are described of four peptides with modified leucine-enkephalin sequences in which the native glycylglycyl segment is replaced by an ω-amino acid residue. o-Nitrophenylthio-ω-amino acids were used as intermediates, and it was found that the derivatives of 4-aminobutyric and 5-amino-valeric acids undergo facile intramolecular cyclization under the influence of N,N'-dicyclohexylcarbodiimide.

  介绍了 合成了四种具有修饰的亮氨酸-脑啡肽序列的肽，其中的原生 ω-氨基酸残基取代。 的衍生物被用作中间体。 4-氨基丁酸和 5-氨基戊酸的衍生物在 N,,B,C,D,E N,N'-二环己基碳二亚胺的影响下发生分子内环化。
• .omega.-Aminocarboxylic acid amides
  申请人：Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.

  公开号：US04218404A1

  公开（公告）日：1980-08-19

  The invention relates to novel .omega.-aminocarboxylic acid amides having the formula (I) ##STR1## wherein A is --SO.sub.2 OH or --OPO(OH).sub.2, R.sup.1 is hydrogen, an acyl group, such as benzoyl, arylsulfonyl, alkoxycarbonyl, cycloalkoxycarbonyl or aralkoxycarbonyl group or an aralkoxycarbonyl group having a halogen, alkoxy, nitro, phenylazo or alkoxyphenylazo substituent, alkyl-substituted aryloxycarbonyl or carbonyl, R.sup.2 is hydrogen or a carbonyl group, with the proviso that when R.sup.1 and R.sup.2 each stand for carbonyl, the two carbonyl groups form a ring through an intervening o-phenylene, alkylene or vinylene group when A is --SO.sub.2 OH and R.sup.1 is an acyl group such as benzoyl, aryl sulfonyl, alkoxy-carbonyl, cycloalkoxycarbonyl or aryloxycarbonyl group or an aralkoxy carbonyl group having a halogen, alkoxy, nitro, phenylozo or alkoxyphenylazo substituent or an alkyl-substituted aryloxycarbonyl group or carbonyl group, R.sup.2 is hydrogen or a carbonyl group, with the proviso that when R.sup.1 and R.sup.2 each stand for carbonyl, the two carbonyl groups form a ring through an intervening o-phenylene, alkylene or vinylene group when A is --O--P--O(OH).sub.2 and n is equal to 2 or 3, and salts of the above compounds, furthermore to a process for the preparation thereof. The novel compounds according to the invention possess valuable pharmacological effects in reducing blood sugar levels or can be applied as intermediate in the synthesis of biologically active compounds.

  本发明涉及具有以下式子（I）的新型ω-氨基羧酸酰胺：其中A为--SO2OH或--OPO(OH)2，R1为氢、酰基、如苯甲酰基、芳烷磺酰基、烷氧羰基、环烷氧羰基或芳基烷氧羰基或具有卤素、烷氧基、硝基、苯偶氮或烷氧基苯偶氮取代基的芳基烷氧羰基或羰基、R2为氢或羰基，但当R1和R2均为羰基时，当A为--SO2OH且R1为酰基，如苯甲酰基、芳烷磺酰基、烷氧羰基、环烷氧羰基或芳基烷氧羰基或具有卤素、烷氧基、硝基、苯偶氮或烷氧基苯偶氮取代基的芳基烷氧羰基或羰基时，两个羰基通过介于o-苯撑、烷基或乙烯基的环形结构形成；但当A为--O--P--O(OH)2且n等于2或3时，R1为苯甲酰基、芳烷磺酰基、烷氧羰基、环烷氧羰基或芳基烷氧羰基或具有卤素、烷氧基、硝基、苯偶氮或烷氧基苯偶氮取代基的芳基烷氧羰基或羰基，R2为氢或羰基，但当R1和R2均为羰基时，两个羰基通过介于o-苯撑、烷基或乙烯基的环形结构形成。本发明还涉及上述化合物的盐，并提供了一种制备它们的方法。根据本发明的新型化合物具有降低血糖水平的有价值的药理作用，或可用作生物活性化合物合成中间体。
• Reactions of  -aminopropionic acid N"-acylhydrazides with carbonyl compounds
  作者：G. A. Smirnov、E. P. Sizova、O. A. Luk"yanov

  DOI：10.1023/b:rucb.0000035649.77800.28

  日期：2004.3

  The reactions of β-aminopropionic acid N"-acylhydrazides with aromatic and heterocyclic aldehydes and acetone afford compounds that exist in solutions predominantly as mixtures of 2-substituted 3-acylaminotetrahydropyrimidin-4-ones (ATHP) and tautomeric Schiff"s bases. These compounds in the crystalline state probably have structures of ATHP. The ratio of tautomers depends on the type of substituent

  β-氨基丙酸 N"-酰基酰肼与芳香族和杂环醛和丙酮的反应产生的化合物主要以 2-取代的 3-酰基氨基四氢嘧啶-4-酮 (ATHP) 和互变异构席夫碱的混合物形式存在于溶液中。这些结晶状态的化合物可能具有ATHP的结构。互变异构体的比例取决于芳环和溶剂中取代基的类型。2-aryl-3-benzamidotetrahydropyrimidin-4-ones 与羧酸或磺酸氯化物的反应得到 1-acyl-和 1-tosyl-3-benzamidotetrahydropyrimidin-4-ones 的衍生物。