(R)-吡咯烷-2-乙酸 | 61350-65-0

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (R)-吡咯烷-2-乙酸
• 英文名称: (R)-2-(pyrrolidin-2-yl)acetic acid
• 英文别名: (2R)-carboxymethylpyrrolidine；pyrrolidine-2-yl-acetic acid；(R)-homoproline；(R)-Homoprolin；homoproline；2-[(2R)-pyrrolidin-1-ium-2-yl]acetate
• CAS: 61350-65-0
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: ADSALMJPJUKESW-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280
• 危险性描述：
  H302,H317

反应信息

• 作为反应物：
  描述：

  (R)-吡咯烷-2-乙酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (2R)-2-(2-[4-(2-methoxyphenyl)piperazin-1-yl]-2-oxoethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of potential 5-HT7 receptor PET radiotracers

  摘要：

  Brain serotonin 7 receptor (5-HT7) is involved in several mood disorders and drug candidates targeting this subtype are currently in development. Positron emission tomography (PET) is a molecular imaging modality offering great promise for accelerating the process from preclinical discovery to clinical phases. As no PET radiopharmaceutical has yet been used successfully to study the 5-HT7 receptor in vivo, our objective is to develop the first 5-HT7 fluorine-18 labeled radiotracer.Four structural analogs of SB269970, a specific 5-HT7 receptor antagonist, divided in FP3 series and FPMP series were synthesized. Their antagonist effects were investigated by cellular functional assay. Nitro-precursors of these analogs were radiolabeled via a [F-18(-)]nucleophilic substitution and in vitro autoradiographies were performed in rat brain.Chemical and radiochemical purities of fluorine radiotracers were >99% with specific activities in 40 -129 GBq/mu mole range. The four derivates presented antagonism potencies toward 5-HT7 receptors (PKB) between 7.8 and 8.8. The four PET radiotracers had suitable characteristic for 5-HT7 receptor probing in vitro even if the FP3 series seemed to be more specific for this receptor. These results encourage us to pursue in vivo studies. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.010
• 作为产物：
  描述：

  N-<(S)-3-Phenyl-2-(2,2-dimethylpropionyloxy)-propionyl>-(R)-pyrrolidin-2-ylessigsaeure 在 硫酸 作用下， 反应 15.0h， 以59%的产率得到(R)-吡咯烷-2-乙酸
  参考文献：
  名称：

  Asymmetrische elektrophile α-Amidoalkylierung, 4. Mitt.: Erzeugung und Abfangreaktionen 手性 N-Acylpyrrolidiniumionen

  摘要：

  Die Pyrrolderivate 1, 6 und 10 werden unter TiCl4-Katalysestereoselektiv mil dem Silylenolether 3 zu 2-substituierten Pyrrolidinamiden umgesetzt。6 sowie 10 (nach HCl-Addition = >11) sind noch bei -78°C reaktiv, wobei die Reaktion von 10 die von 6 in Ausbeute und Stereoselektivität übertrifft。

  DOI：

  10.1002/ardp.19893220209

文献信息

• CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS
  申请人：Obrecht Daniel

  公开号：US20120202821A1

  公开（公告）日：2012-08-09

  Conformationally restricted, spatially defined 12-30 membered macrocyclic ring systems of type (I) are constituted by three distinct building blocks: an aromatic template a, a conformation modulator b and a spacer moiety c as detailed in the description and the claims. Macrocycles of type (I) are readily manufactured by parallel synthesis or combinatorial chemistry. They are designed to interact with specific biological targets. In particular, they show agonistic or antagonistic activity on the motilin receptor (MR receptor), on the serotonin receptor of subtype 5-HT 2B (5-HT 2B receptor), and on the prostaglandin F2•receptor (FP receptor). They are thus potentially useful for the treatment of hypomotility disorders of the gastrointestinal tract such as diabetic gastroparesis and constipation type irritable bowl syndrome; of CNS related diseases like migraine, schizophrenia, psychosis or depression; of ocular hypertension such as associated with glaucoma and preterm labour.

  构象受限、空间定义的12-30环大环环系统(I型)由三个不同的构建模块组成：芳香模板a、构象调节剂b和间隔基团c，如详细描述和索赔中所述。类型(I)的大环可通过并行合成或组合化学方法轻松制备。它们被设计用于与特定生物靶点相互作用。特别是，它们在胃动素受体(MR受体)、5-HT2B亚型的5-羟色胺受体(5-HT2B受体)和前列腺素F2受体(FP受体)上显示出激动或拮抗活性。因此，它们潜在地可用于治疗胃肠道低动力障碍，如糖尿病性胃轻瘫和便秘型肠易激综合征；中枢神经系统相关疾病，如偏头痛、精神分裂症、精神病或抑郁症；眼压增高，如青光眼和早产。
• Improved Protocol for Asymmetric, Intramolecular Heteroatom Michael Addition Using Organocatalysis: Enantioselective Syntheses of Homoproline, Pelletierine, and Homopipecolic Acid
  作者：Erik C. Carlson、Lauren K. Rathbone、Hua Yang、Nathan D. Collett、Rich G. Carter

  DOI：10.1021/jo800749t

  日期：2008.7.1

  indoline, and piperidine rings using an organocatalyzed, intramolecular heteroatom Michael addition is described. Application to the enantioselective synthesis of homoproline, homopipecolic acid, and pelletierine has been accomplished.

  描述了使用有机催化的分子内杂原子迈克尔加成构建对映体富集的吡咯烷、二氢吲哚和哌啶环的改进方案。已完成对高脯氨酸、高哌可酸和匹莱林的对映选择性合成的应用。
• SUBSTITUTED BENZHYDRYLETHERS
  申请人：Gant Thomas G.

  公开号：US20090203763A1

  公开（公告）日：2009-08-13

  Disclosed herein are substituted benzhydrylethers of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and methods of their use thereof.

  本文揭示了式I的取代苯基乙醚，其制备方法，药物组合物以及它们的使用方法。
• RAPAFUCIN DERIVATIVE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：The Johns Hopkins University

  公开号：US20210094933A1

  公开（公告）日：2021-04-01

  The present disclosure provides macrocyclic compounds inspired by the immunophilin ligand family of natural products FK506 and rapamycin. The generation of a Rapafucin library of macrocyles that contain FK506 and rapamycin binding domains should have great potential as new leads for developing drugs to be used for treating diseases.

  本公开提供了受免疫蛋白配体家族FK506和雷帕霉素天然产物启发的大环化合物。生成包含FK506和雷帕霉素结合结构域的Rapafucin大环化合物库，应具有作为治疗疾病新药的潜力。
• BETA-HAIRPIN PEPTIDOMIMETICS AS SELECTIVE ELASTASE INHIBITORS
  申请人：POLYPHOR AG

  公开号：US20160333053A1

  公开（公告）日：2016-11-17

  β-Hairpin peptidomimetics of the general formula cyclo(-Xaa 1 -Xaa 2 -Thr 3 -Xaa 4 -Ser 5 -Xaa 6 -Xaa 7 -Xaa 8 -Xaa 9 -Xaa 10 -Xaa 11 -Xaa 12 -Xaa 13 -) and pharmaceutically acceptable salts thereof, with Xaa 1 , Xaa 2 , Xaa 4 , Xaa 6 , Xaa 7 , Xaa 8 , Xaa 9 , Xaa 10 , Xaa 11 , Xaa 12 and Xaa 13 being amino acid residues of certain types which are defined in the description and the claims, have elastase inhibitory properties, especially against human neutrophil elastase, and can be used for preventing infections or diseases related to such infections in healthy individuals or for slowing infections in infected patients. The compounds of the invention can further be used where cancer, or immunological diseases, or pulmonary diseases, or cardiovascular diseases, or neurodegenerative diseases, or inflammation, or diseases related to inflammation, are mediated or resulting from elastase activity. These peptidomimetics can be manufactured by a process which is based on a mixed solid- and solution phase synthetic strategy.

  β-头发环肽类似物的一般公式为cyclo(-Xaa1-Xaa2-Thr3-Xaa4-Ser5-Xaa6-Xaa7-Xaa8-Xaa9-Xaa10-Xaa11-Xaa12-Xaa13-)及其药学上可接受的盐，其中Xaa1、Xaa2、Xaa4、Xaa6、Xaa7、Xaa8、Xaa9、Xaa10、Xaa11、Xaa12和Xaa13是在描述和权利要求中定义的某些类型的氨基酸残基，具有弹性酶抑制性质，特别是对人类中性粒细胞弹性蛋白酶，可用于预防健康个体中与此类感染相关的感染或疾病，或者用于减缓感染患者中的感染。该发明的化合物还可用于癌症、免疫性疾病、肺部疾病、心血管疾病、神经退行性疾病、炎症或与炎症相关的疾病由弹性酶活性介导或由此导致的情况。这些肽类似物可以通过基于混合固相和溶液相合成策略的过程制造。