1-carbamoylpyrrolidine-2-carboxylic acid | 173243-90-8

• 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: 1-carbamoylpyrrolidine-2-carboxylic acid
• 英文别名: (+/-)-N-carbamoylproline；N-carbamoyl-DL-proline；N-carbamoylproline
• CAS: 173243-90-8
• 化学式: C₆H₁₀N₂O₃
• mdl: MFCD03936200
• 分子量: 158.157
• InChiKey: RTNFBJXLYMERBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺二乙基缩醛 、 1-carbamoylpyrrolidine-2-carboxylic acid 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以38%的产率得到N,N-dimethyl-N'-(2-ethoxycarbonylpyrrolidinyl-1-acetyl)formamidine
  参考文献：
  名称：

  Nootropic activity of ureidoacids and thiohydantoins

  摘要：

  DOI：

  10.1007/bf00764413
• 作为产物：
  描述：

  L-瓜氨酸 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 24.0h， 以20%的产率得到(2S)-5-(carbamoylamino)-2-hydroxypentanoic acid
  参考文献：
  名称：

  Gouesnard, Jean-Paul, Bulletin de la Societe Chimique de France, 1989, # 1, p. 88 - 94

  摘要：

  DOI：

文献信息

• [EN] 2-PYRROLIDINE PHENYLHYDRAZIDES ANTIBACTERIAL AGENTS<br/>[FR] AGENTS ANTIBACTÉRIENS À BASE DE 2-PYRROLIDINE PHÉNYLHYDRAZIDES
  申请人：ABAC THERAPEUTICS S L

  公开号：WO2018020004A1

  公开（公告）日：2018-02-01

  2-Pyrrolidine phenylhydrazides antibacterial agents The present invention relates to 2-pyrrolidine phenylhydrazide compounds of formula (I), which are selective antibacterials specifically agalnstAcineto barter baumannii.The invention also relates to their therapeutic use as antibacterials, to a process for their preparation and to pharmaceutical compositions containing them.

  2-吡咯烷基苯基肼抗菌剂。本发明涉及式(I)的2-吡咯烷基苯基肼化合物，这些化合物是针对鲍曼不动杆菌的选择性抗菌剂。本发明还涉及它们作为抗菌剂的治疗用途，以及它们的制备方法和含有它们的药物组合物。
• Enzyme-catalyzed enantiomeric resolution of N-Boc-proline as the key-step in an expeditious route towards RAMP
  作者：Masayuki Kurokawa、Takeyuki Shindo、Masumi Suzuki、Nobuyoshi Nakajima、Kohji Ishihara、Takeshi Sugai

  DOI：10.1016/s0957-4166(03)00210-6

  日期：2003.5

  For the preparation of both enantiomers of N-carbamoyl-2-methoxymethylpyrrolidine, the precursors of Enders’ chiral auxiliaries, SAMP and RAMP, enzyme-catalyzed kinetic resolution of racemic N-carbamoyl, N-Boc, N-Cbz proline esters and prolinols were examined. B. licheniformis protease (subtilisin) preferentially hydrolyzed the (R)-carbamoylproline ester with an enantiomeric ratio (E) of 10. To a hydrophobic

  对于两种对映体的制备Ñ -氨基甲酰基-2-甲氧基甲基，的恩德斯手性助剂，SAMP和RAMP的前体，酶催化的外消旋的动力学拆分Ñ -氨基甲酰基，Ñ -Boc，Ñ -Cbz脯氨酸酯和脯氨醇为检查。地衣芽孢杆菌蛋白酶（枯草杆菌蛋白酶）优先水解（R）-氨基甲酰基脯氨酸酯，对映体比率（E）为10。枯草杆菌蛋白酶对疏水性N -Cbz脯氨酸酯显示出较低的选择性（E = 2.8），相反，纯化的蛋白酶（同工酶A）对（S）-对映体（E= 13.6）。在实际意义上，南极衣原体脂肪酶B（Chirazyme L-2）可有效水解E> 100的N -Boc和N -Cbz衍生物。（R）-N-氨基甲酰基-2-甲氧基甲基吡咯烷酮的ee通过在N -Boc-脯氨醇阶段重结晶而提高到> 99.9％，该阶段衍生自（R）-N -Boc-脯氨酸甲酯（98.7 ％ee）通过外消旋底物的制备规模的酶催化拆分（49％收率）。
• Synthesis, Crystal Structure and Hydrogen-Bonding Patterns in (RS)-1-Carbamoyl Pyrrolidine-2-Carboxylic Acid
  作者：Gerzon E. Delgado、Luis E. Seijas、Asiloé J. Mora、Teresa González、Alexander Briceño

  DOI：10.1007/s10870-011-0259-4

  日期：2012.4

  The title compound, N-carbamoyl-dl-proline, C6H10N2O3, crystallizes in the triclinic P-1 space group with unit cell parameters a = 7.610 (4) Å, b = 9.259 (5) Å, c = 11.749 (7) Å, α = 110.294 (11)°, β = 101.304 (13)°, γ = 91.391 (16)°, with two crystallographically independent molecules in the asymmetric unit. The ureido and carboxyl groups are equatorial and axial to the pyrrolidine rings, respectively. The pyrrolidine rings adopt envelope and twisted conformations in the residue A and B, respectively. The molecules are joined by N–H···O and O–H···O hydrogen bonds into cyclic structures with graph set R 2 2 (8), forming infinite chains parallel to the cb plane with graph set C 2 2 (14), that are further connected via N–H···O hydrogen bonds into a three-dimensional network. The molecules of N-carbamoyl-dl-proline are joined by N–H···O and O–H···O hydrogen bonds into cyclic structures with graph set R 2 2 (8), forming infinite ribbons parallel to the cb plane with graph-set C 2 2 (14), that are further connected via N–H···O hydrogen bonds into a three-dimensional network.

  标题化合物 N-氨基甲酰基-dl-脯氨酸（C6H10N2O3）在三linic P-1 空间群中结晶，单胞参数 a = 7.610 (4) Å, b = 9.259 (5) Å, c = 11.749 (7) 埃，α = 110.294 (11)°，β = 101.304 (13)°，γ = 91.391 (16)°，不对称单元中有两个晶体学上独立的分子。脲基和羧基分别位于吡咯烷环的赤道和轴向。吡咯烷环在残基 A 和 B 中分别呈包络和扭曲构象。这些分子通过 N-H-O 和 O-H-O 氢键连接成图集为 R 2 2 (8) 的环状结构，形成图集为 C 2 2 (14) 的平行于 cb 平面的无限链，再通过 N-H-O 氢键连接成三维网络。N-carbamoyl-dl-proline 分子通过 N-H-O 和 O-H-O 氢键连接成图集为 R 2 2 (8) 的环状结构，形成平行于图集为 C 2 2 (14) 的 cb 平面的无限带，再通过 N-H-O 氢键连接成三维网络。
• CAROTENOID DERIVATIVE, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICALLY ACCEPTABLE ESTER OR AMIDE THEREOF
  申请人：Fuji Chemical Industry Co., Ltd.

  公开号：EP3147279A1

  公开（公告）日：2017-03-29

  The object of the present invention is to find a carotenoid compound that is excellent in water solubility. A carotenoid derivative having a formula (I): wherein X represents a carbonyl group or a methylene group, one of R1 and R2 represents (a) or (b) and the other represents (a), (b), (c) or a hydrogen atom: (a): -CO-A-B-D wherein A represents an alkylene group an alkenylene group, etc., B represents a formula of -S(O)n- or a formula of -NR4CONR5- and D represents a hydrogen atom, a carboxy group, etc., (b): -CO-E-F wherein E represents an alkylene group or a formula of -NR3- wherein R3 represents (a1) a hydrogen atom, (b1) an alkyl group etc., and F represents a sulfo group and (c): -CO-G wherein G represents a hydrogen atom, an alkyl group, 1 etc., a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable ester or amide thereof.

  本发明的目的是找到一种水溶性极佳的类胡萝卜素化合物。 一种类胡萝卜素衍生物具有式（I）： 其中 X代表羰基或亚甲基，R1和R2中的一个代表(a)或(b)，另一个代表(a)、(b)、(c)或氢原子： (a):-其中 A 代表亚烯基、烯基等，B 代表-S(O)n- 或-NR4CONR5-，D 代表氢原子、羧基等、 (b): -CO-E-F 其中 E 代表亚烷基或式 -NR3- 其中 R3 代表 (a1) 氢原子、(b1) 烷基等，F 代表磺基和 (c):-CO-G，其中 G 代表氢原子、烷基、1 等、 其药学上可接受的盐，或其药学上可接受的酯或酰胺。
• 2-pyrrolidine phenylhydrazides antibacterial agents
  申请人：ABAC THERAPEUTICS, S.L

  公开号：US10919851B2

  公开（公告）日：2021-02-16

  2-Pyrrolidine phenylhydrazides antibacterial agents The present invention relates to 2-pyrrolidine phenylhydrazide compounds of formula (I), which are selective antibacterials specifically against Acinetobacter baumannii. The invention also relates to their therapeutic use as antibacterials, to a process for their preparation and to pharmaceutical compositions containing them.

  2-Pyrrolidine phenylhydrazides antibacterial agents 本发明涉及式 (I) 的 2-Pyrrolidine phenylhydrazide 化合物，它们是专门针对鲍曼不动杆菌（Acinetobacter baumannii）的选择性抗菌剂。本发明还涉及它们作为抗菌剂的治疗用途、制备方法以及含有它们的药物组合物。