N-甲基-3-(1-吡咯烷)-1-丙胺 | 99114-68-8

• 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: N-甲基-3-(1-吡咯烷)-1-丙胺
• 中文别名: N-甲基-1-吡咯烷丙胺
• 英文名称: N-<3-(methylamino)propyl>pyrrolidine
• 英文别名: N-methyl-3-(1-pyrrolidinyl)-1-propanamine；N-Methyl-3-(pyrrolidin-1-yl)propan-1-amine；N-methyl-3-pyrrolidin-1-ylpropan-1-amine
• CAS: 99114-68-8
• 化学式: C₈H₁₈N₂
• mdl: MFCD09055238
• 分子量: 142.244
• InChiKey: PBKBNZLWSVHLAG-UHFFFAOYSA-N

物化性质

• 沸点：
  200.3±8.0℃ (760 Torr)
• 密度：
  0.893±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  70.4±9.4℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  N-甲基-3-(1-吡咯烷)-1-丙胺 在 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3,4-dichloro-N-methyl-N-[2-[methyl(3-pyrrolidin-1-ylpropyl)amino]ethyl]benzamide
  参考文献：
  名称：

  A new approach to the design of .sigma.-2-selective ligands: synthesis and evaluation of N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)ethylamine-related polyamines at .sigma.-1 and .sigma.-2 receptor subtypes

  摘要：

  A series of polyamines based on the high affinity sigma receptor ligand N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)ethylamine (3) were developed and evaluated for their binding characteristics at sigma-1 and sigma-2 receptor subtypes. The data indicated that a considerable degree of structural variation is possible while still retaining nanomolar affinity at a receptors; As the structure of the polyamines was varied, their binding at sigma-1 and sigma-2 subtypes showed quite different and in some cases opposite trends, supporting the belief that these are pharmacologically distinct entities. Polyamines containing two nitrogen atoms showed optimal binding at both sigma-1 and sigma-2 receptor subtypes. Although additional nitrogen atoms resulted in decreased affinity at sigma-1 and sigma-2 subtypes, an increase in selectivity for sigma-2 subtypes was evident; the parent 3 showed greater selectivity for sigma-1 subtypes. Internitrogen spacings had a large effect on binding affinity and subtype selectivity. For example, the difference between N-[3-(1-pyrrolidinyl)propyl]-N'-(3,4-dichlorobenzyl)-N,N'-dimethylethylenediamine (8) [K-i = 29.9 nM at sigma-1 receptor and 18.3 nM at alpha-2 receptor] to N-[3-(1-pyrrolidinyl)propyl]-N'-(3,4-dichlorobenzyl)-N/N'-dimethylethylenedi- amine (10) [K-i = 1.49 nM at sigma-1 receptor and 12.1 nM at sigma-2 receptor] illustrates the importance of internitrogen spacing. Triamines 11 and 13 [K-i(sigma-2)/K-i(sigma-1) = 0.19 and 0.10, respectively] containing the N-N-N-Ar spacings 3-3-2 and 4-4-2, proved to be the most sigma-2 subtype selective of the 15 polyamines examined in this study. The N-N-N spacings appear to be an important factor in their sigma-2 subtype selectivity. These compounds will serve as templates in the design of still further sigma-2 subtype selective ligands. The pyrrolidine ring (present in most of the polyamines tested in this series) proved to be an important recognition site for a receptor binding activity. Furthermore, alkyl substitution also appears to be important since the stripped down polyamines N-[2-(3,4-dichlorophenyl)ethyl]ethylenediamine (15) and N-1-[2-(3,4-dichlorophenyl)ethyl] diethylenetriamine (16) exhibited relatively low binding affinity.

  DOI：

  10.1021/jm00028a016
• 作为产物：
  描述：

  1-(3-氨基丙基)吡咯烷 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-甲基-3-(1-吡咯烷)-1-丙胺
  参考文献：
  名称：

  一类新型的N-（芳基乙基）-N-烷基-2-（1-吡咯烷基）乙胺的合成，表征和生物学评估：结构要求和对sigma受体的结合亲和力。

  摘要：

  通过合成和测试零件结构，N- [2-（3,4-二氯苯基）乙基] -N-甲基-2-（1-吡咯烷基）乙基胺（3）源自我们先前报道的高亲和力σ受体配体（1S，2R）-（-）-N- [2-（3,4-二氯苯基）-乙基] -N-甲基-2-（1-吡咯烷基）环己胺[（-）-2]和（+）-参见图2，我们已经鉴定出一类新型的对[3H]-（+）-3-PPP标记的σ受体具有特异性的超强（亚纳摩尔亲和力）σ配体。测试3从豚鼠脑膜置换[3H]-（+）-3-PPP的能力时，其Ki值为0.34 nM，优于其母体化合物（-）-2（Ki = 1.3 nM）和（+）-2（Ki = 6.0 nM）。与3相关的其他化合物，例如N- [2-（3,4-二氯苯基）乙基] -N-甲基-2-（1-高哌啶基）乙胺（19）的Ki = 0.17 nM [（3H]-（+ ）-3-PPP）。通过以多种不同方式操纵该结构来检查3的高sigma受体亲和力

  DOI：

  10.1021/jm00079a004

文献信息

• Structure–activity relationship studies of SETD8 inhibitors
  作者：Anqi Ma、Wenyu Yu、Yan Xiong、Kyle V. Butler、Peter J. Brown、Jian Jin

  DOI：10.1039/c4md00317a

  日期：——

  Comprehensive SAR studies of the first substrate-competitive SETD8 inhibitor led to the discovery of interesting SAR trends and novel analogs.

  对第一个底物竞争性SETD8抑制剂的全面SAR研究揭示了有趣的SAR趋势和新颖的类似物。
• Novel pyridine derivative and pyrimidine derivative
  申请人：Matsushima Tomohiro

  公开号：US20050277652A1

  公开（公告）日：2005-12-15

  A compound represented by the following formula, a salt thereof or a hydrate of the foregoing has an excellent hepatocyte growth factor receptor (HGFR) inhibitory activity, and exhibits anti-tumor activity, angiogenesis inhibitory activity and cancer metastasis inhibitory activity. [R 1 represents C 1-6 alkyl or the like; R 2 and R 3 represent hydrogen; R 4 , R 5 , R 6 , and R 7 may be the same or different and each represents hydrogen, halogen, C 1-6 alkyl or the like; R 8 represents hydrogen or the like; R 9 represents C 1-6 alkyl or the like; V 1 represents oxygen or the like; V 2 represents oxygen or sulfur; W represents —NH— or the like; X represents —CH═, nitrogen or the like; and Y represents oxygen or the like.]

  以下化合物的分子式，其盐或前述水合物具有出色的肝细胞生长因子受体（HGFR）抑制活性，并表现出抗肿瘤活性、抑制血管生成活性和抑制癌转移活性。 [R 1 代表C 1-6 烷基或类似物；R 2 和R 3 代表氢；R 4 ，R 5 ，R 6 和R 7 可以相同也可以不同，每个代表氢、卤素、C 1-6 烷基或类似物；R 8 代表氢或类似物；R 9 代表C 1-6 烷基或类似物；V 1 代表氧或类似物；V 2 代表氧或硫；W代表—NH—或类似物；X代表—CH═、氮或类似物；Y代表氧或类似物。]
• [EN] TRIAZOLYL-SUBSTITUTED PYRIDYL COMPOUNDS USEFUL AS KINASE INHIBITORS<br/>[FR] COMPOSÉS PYRIDYLES À SUBSTITUTION TRIAZOLYLE UTILES COMME INHIBITEURS DE KINASES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2013106614A1

  公开（公告）日：2013-07-18

  Compounds having the following formula:(I) wherein:A is an optionally substiuted triazole, or a stereoisomer or a pharmaceutically-acceptable salt thereof, are useful as kinase modulators, including IRAK-4 modulation.

  具有以下公式的化合物：（I）其中：A 是一个可选地取代的三唑环，或者其立体异构体或药用可接受的盐，可用作激酶调节剂，包括 IRAK-4 调节。
• [EN] SUBSTITUTED-IMIDAZO[1,2-B]PYRIDAZINES AS MKNK1 INHIBITORS<br/>[FR] IMIDAZO[1,2-B] PYRIDAZINES SUBSTITUÉES COMME INHIBITEURS DE MKNK1
  申请人：BAYER PHARMA AG

  公开号：WO2014128093A1

  公开（公告）日：2014-08-28

  The present invention relates to amido-substituted imidazopyridazine compounds of general formula (I): (Ia) (Ib) (Ic) (Id) in which A, Y, R1, R2, R3, R4 and n are as defined in the claims, to methods of preparing said compounds, to intermediate compounds useful for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of a hyper-proliferative and/or angiogenesis disorder, as a sole agent or in combination with other active ingredients.

  本发明涉及一般式(I)的酰胺取代咪唑吡啶化合物：(Ia) (Ib) (Ic) (Id)，其中A、Y、R1、R2、R3、R4和n如权利要求中所定义，涉及制备所述化合物的方法，用于制备所述化合物的有用中间体化合物，包含所述化合物的药物组合物和组合物，以及利用所述化合物制造用于治疗或预防疾病的药物组合物，特别是用作唯一药剂或与其他活性成分组合使用时，用于治疗或预防过度增殖和/或血管生成紊乱的疾病。
• CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS
  申请人：POLYPHOR AG

  公开号：US20150051183A1

  公开（公告）日：2015-02-19

  The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

  公式（I）的构象受限、空间定义的大环环系统由三个不同的分子部分组成：模板A、构象调节剂B和桥C。由这种环系统I描述的大环可通过并行合成或溶液中或固相上的组合化学轻松制造。它们被设计用于与各种特定生物靶标类相互作用，例如在G蛋白偶联受体（GPCR）上的激动或拮抗活性，酶的抑制活性或抗菌活性。特别是，这些大环显示对亚型1的内皮素转化酶（ECE-1）和/或半胱氨酸蛋白酶卡特普辛S（CatS）的抑制活性，和/或作为催产素（OT）受体、促甲状腺释放激素（TRH）受体和/或白三烯B4（LTB4）受体的拮抗剂，和/或作为瘤胃素3（BB3）受体的激动剂，和/或对至少一种细菌菌株显示抗菌活性。因此，它们显示出作为各种疾病药物的巨大潜力。