(3S)-aminopyrrolidine dihydrochloride | 116183-83-6

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3S)-aminopyrrolidine dihydrochloride
• 英文别名: (S)-3-aminopyrrolidine dihydrochloride；(S)-pyrrolidin-3-amine dihydrochloride；3-aminopyrrolidine dihydrochloride；(3S)-3-aminopyrrolidine dihydrochloride；(S)-(+)-3-Aminopyrrolidine DiHCl；(3S)-pyrrolidin-3-amine;hydrochloride
• CAS: 116183-83-6
• 化学式: C₄H₁₀N₂*2ClH
• 分子量: 159.059
• InChiKey: NPPLFOLRHWBLKV-WCCKRBBISA-N

物化性质

• 熔点：
  283°C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.27
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S36
• 海关编码：
  2933990090
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

制备方法与用途

简介

(S)-3-氨基吡咯烷二盐酸盐是氨基吡咯烷衍生物。3?氨基吡咯烷二盐酸盐及其光学异构体是合成大量手性药物的关键中间体。

用途

通过3‑氨基吡咯烷可以用来合成碳青霉烯类抗生素、喹诺酮类抗菌剂、趋化因子调节剂等系列药物。

反应信息

• 作为反应物：
  描述：

  (3S)-aminopyrrolidine dihydrochloride 、 7-chloro-6-fluoro-5-methyl-1-(1,1-dimethylethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid ethyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以59%的产率得到7-<(3S)-3-aminopyrrolidinyl>-1-(1,1-dimethylethyl)-6-fluoro-5-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted 6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids

  摘要：

  A series of 5-substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids have been prepared and tested for their in vitro and in vivo antibacterial activities. The 5-methyl group gave better in vitro activity with the 1-cyclopropyl appendage, but poorer activity with the 1-tert-butyl moiety. With the 1-(2,4-difluorophenyl) substitution, the influence of the 7-cycloalkylamino group was determinant: a (3S)-3-amino-pyrrolidine was shown to enhance greatly the in vitro and in vivo activity of the 5-methyl derivative. Compound 33 (BMY 43748) was selected as a promising candidate for an improved therapeutic agent.

  DOI：

  10.1021/jm00081a013
• 作为产物：
  描述：

  (3S)-3-azido-1-(phenylmethyl)pyrrolidine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 (3S)-aminopyrrolidine dihydrochloride
  参考文献：
  名称：

  Fluoronaphthyridines and -quinolones as antibacterial agents. 5. Synthesis and antimicrobial activity of chiral 1-tert-butyl-6-fluoro-7-substituted-naphthyridones

  摘要：

  A series of novel 7-substituted-1-tert-butyl-6-fluoronaphthyridone-3-carboxylic acids has been prepared. These derivatives are characterized by chiral aminopyrrolidine substituents at the 7 position. In this paper we report the full details of the asymmetric synthesis of this series of compounds. Structure-activity relationship studies indicate that the absolute stereochemistry at the asymmetric centers of the pyrrolidine ring is critical for maintaining good activity. Compounds 60 and 61 (3-amino-4-methylpyrrolidine enantiomers) were selected for preclinical evaluation.

  DOI：

  10.1021/jm00100a028

文献信息

• Syntheses of new pyridonecarboxylic acid derivatives containing 1- or 2-naphthyl substituents at n-1 and their anti-hiv-rt activities
  作者：Yoon-Seok Oh、Sung-Hye Cho

  DOI：10.1002/jhet.5570350104

  日期：1998.1

  A series of new pyridonecarboxylic acid derivatives containing 1- or 2-naphthyl substituents at N-1 were synthesized and their in vitro anti-HIV-RT activities were evaluated. Several compounds in this series showed better activity than Atevirdine.

  合成了一系列在N-1处含有1-或2-萘基取代基的新吡啶酮羧酸衍生物，并对其体外抗HIV-RT活性进行了评估。该系列中的几种化合物显示出比Atevirdine更好的活性。
• Syntheses of new pyridonecarboxylic acid derivatives containing 3-,5- or 6-quinolyl substituents at N-1 and their anti-HIV-RT activities
  作者：Yoon-Seok Oh、Chi-Wbo Lee、Yong-Ho Chung、Sung-June Yoon、Sung- Hye Cho

  DOI：10.1002/jhet.5570350309

  日期：1998.5

  A series of new pyridonecarboxylic acid derivatives containing 3-, 5- or 6-quinolyl substituents at N-1 were synthesized and their in vitro anti-HIV-RT activities were evaluated. Several compounds in this series showed better activity than Atevirdine.

  合成了一系列在N-1处含有3-，5-或6-喹啉基取代基的新吡啶酮羧酸衍生物，并评估了它们的体外抗HIV-RT活性。该系列中的几种化合物显示出比Atevirdine更好的活性。
• Pyridonecarboxylic acid derivatives or salts thereof and antibacterial
  申请人：Wakunaga Seiyaku Kabushiki Kaisha

  公开号：US05910498A1

  公开（公告）日：1999-06-08

  The invention provides a pyridonecarboxylic acid derivative of the following general formula (1): ##STR1## wherein R.sup.1 is a hydrogen atom or carboxy protecting group, R.sup.2 is a nitro or substituted or unsubstituted amino group, R.sup.3 is a halogen atom, each of R.sup.4 and R.sup.5, which may be the same or different, is a hydrogen atom, halogen atom, lower alkyl group or lower alkoxy group, A is a nitrogen atom or --CX.dbd. wherein X is a hydrogen atom, halogen atom, lower alkyl group or lower alkoxy group, and Z is a halogen atom or a saturated cyclic amino group which may have a substituent, or a salt thereof and an antibacterial agent comprising the same.

  该发明提供了以下一般式（1）的吡啶酮羧酸衍生物： 其中R.sup.1是氢原子或羧基保护基，R.sup.2是硝基或取代或未取代的氨基，R.sup.3是卤素原子，R.sup.4和R.sup.5中的每一个，可以相同也可以不同，是氢原子、卤素原子、低烷基基团或低烷氧基团，A是氮原子或--CX.dbd.，其中X是氢原子、卤素原子、低烷基基团或低烷氧基团，Z是卤素原子或饱和环状氨基团，可能带有取代基，或其盐以及包含其的抗菌剂。
• Chiral Substitution on Spaced Cations Lead to Improved Properties and Reversible Phase Transition, Broadband Emission in Parent Compound (3APr)PbBr₄
  作者：Ming‐Yang Wan、Yun‐Zhi Tang、Yu‐Hui Tan、Yi‐Luo Li、Fang‐Xin Wang、Juan Liao、Li‐Juan Wang

  DOI：10.1002/ejic.202300476

  日期：2023.11.2

  Hybrid organic‐inorganic perovskites (HOIP) due to their excellent optoelectronic properties and flexible structure have attracted enthusiastic interest. In particular, introducing chirality is a method to enhance compound performance. Herein, we report a multifunctional compound: (3APr)PbBr₄ (1) (3APr=3‐Pyrrolidinamine) and corresponding enantiomer R and S‐(3APr)PbBr₄ (R/S‐2). Compound 1 show reversible solid‐state phase transition, step‐like dielectric anomaly and broadband yellow emission under uv light excitation. Accompany with phase transition, structure dimension transition from 2D to 1D without space group change. Through introduce chirality, the R/S‐2 display mirror image 1D structural relationship, increased quantum yield from 3.43 % (1) to 13.65 % (R/S‐2) and exhibits corresponding CD signals. Then combine to first‐principles analysis, it was found that fluorescence is attributed to the formation of instantaneous defects during excitation, leading to the formation of self‐trapped excitons (STEs). This finding will further promote the development of multifunctional compound and the study of chiral substitution enhance compound properties.

  摘要杂化有机-无机包覆晶石（HOIP）因其优异的光电性能和灵活的结构而备受关注。其中，引入手性是提高化合物性能的一种方法。在此，我们报告了一种多功能化合物：(3APr)PbBr4 (1) （3APr=3-吡咯烷胺）以及相应的对映体 R 和 S-(3APr)PbBr4 (R/S-2)。化合物 1 在紫外光激发下显示出可逆固态相变、阶梯状介电异常和宽带黄色发射。伴随着相变，化合物的结构尺寸也从二维转变为一维，且没有空间群变化。通过引入手性，R/S-2 显示出镜像一维结构关系，量子产率从 3.43 %（1）提高到 13.65 %（R/S-2），并显示出相应的光盘信号。然后结合第一原理分析发现，荧光是由于激发过程中瞬时缺陷的形成，导致自俘获激子（STE）的形成。这一发现将进一步促进多功能化合物的开发和手性取代增强化合物性能的研究。
• Mepyramine–JNJ7777120-hybrid compounds show high affinity to hH1R, but low affinity to hH4R
  作者：Eva Wagner、Hans-Joachim Wittmann、Sigurd Elz、Andrea Strasser

  DOI：10.1016/j.bmcl.2011.09.001

  日期：2011.11

  In literature, a synergism between histamine H-1 and H-4 receptor is discussed. Furthermore, it was shown, that the combined application of mepyramine, a H-1 antagonist and JNJ7777120, a H-4 receptor ligand leads to a synergistic effect in the acute murine asthma model. Thus, the aim of this study was to develop new hybrid ligands, containing one H-1 and one H-4 pharmacophor, connected by an appropriate spacer, in order to address both, H1R and H4R. Within this study, we synthesized nine hybrid compounds, which were pharmacologically characterized at hH(1)R and hH(4)R. The new compounds revealed (high) affinity to hH(1)R, but showed only low affinity to hH(4)R. Additionally, we performed molecular dynamic studies for some selected compounds at hH(1)R, in order to obtain information about the binding mode of these compounds on molecular level. (C) 2011 Elsevier Ltd. All rights reserved.