N-methyl-4-(1-pyrrolidinyl)-2-butynylamine | 75858-55-8

• 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: N-methyl-4-(1-pyrrolidinyl)-2-butynylamine
• 英文别名: N-methyl-4-(1-pyrrolidynyl)-2-butynylamine；N-methyl-4-(1-pyrrolidinyl)-2-butynamine；2-Butyn-1-amine, N-methyl-4-(1-pyrrolidinyl)-；N-methyl-4-pyrrolidin-1-ylbut-2-yn-1-amine
• CAS: 75858-55-8
• 化学式: C₉H₁₆N₂
• 分子量: 152.239
• InChiKey: MHUJGFJOUGZSSK-UHFFFAOYSA-N

物化性质

• 沸点：
  59 °C(Press: 0.01 Torr)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-4-(1-pyrrolidinyl)-2-butynylamine 在 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  功能化同类药物设计新毒蕈碱剂。N-甲基-N- [4-（1-吡咯烷基）-2-丁炔基]酰胺的合成和药理评价。

  摘要：

  使用功能化的同类方法设计毒蕈碱胆碱能受体（mAChRs）的配体。制备了一系列N-甲基-4-（1-吡咯烷基）-2-丁炔胺的ω-官能化烷基酰胺（22）作为UH 5 [N-甲基-N- [4-（1-吡咯烷基）]的官能化类似物-2-丁炔基]乙酰胺]，一种与氧代雷莫林有关的毒蕈碱激动剂。中间体22与一系列Boc保护的ω-氨基酸偶联，并且将所得的酰胺脱保护并酰化。中间体22也用琥珀酸酐酰化并衍生化。体外评估了合成中间体和最终化合物对表达m3AChRs的SK-N-SH人成神经细胞瘤细胞中磷脂酰肌醇周转的影响，以及对仅表达m4AChRs的NG108-15神经母细胞瘤x胶质瘤细胞中环状AMP产生的影响。 。还从这些细胞系的每一个中在膜制品中测量了[3 H] -N-甲基东pol碱的置换。甘氨酸和β-丙氨酸的结合物是m4AChRs的激动剂，对m3AChRs几乎没有活性。通常，随着ω-氨基烷基同类物链长的增加，从m3-和m4AChRs取代[3H]

  DOI：

  10.1021/jm00164a044
• 作为产物：
  描述：

  N,N,N',N',N''-Pentamethyl-N''-[4-(pyrrolidin-1-yl)but-2-yn-1-yl]phosphoric triamide 在 盐酸 作用下， 反应 11.0h， 以94%的产率得到N-methyl-4-(1-pyrrolidinyl)-2-butynylamine
  参考文献：
  名称：

  Corbel, Bernard; Paugam, Jean-Paul; Sturtz, Georges, Canadian Journal of Chemistry, 1980, vol. 58, # 20, p. 2183 - 2188

  摘要：

  DOI：

文献信息

• Urea and 2-imidazolidone derivatives of the muscarinic agents oxotremorine and N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide
  作者：Bjoern M. Nilsson、Hugo M. Vargas、Uli Hacksell

  DOI：10.1021/jm00095a025

  日期：1992.8

  Some urea and 2-imidazolidone analogues of the muscarinic agents oxotremorine (1) and N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide [10; BM-5] have been synthesized and assayed for muscarinic and antimuscarinic activity on the isolated guinea pig ileum. The new compounds (15-24) were found to be muscarinic agonists, partial agonists, or antagonists. The compounds were also tested for in vitro

  毒蕈碱剂oxotremorine（1）和N-甲基-N-（1-甲基-4-吡咯烷基-2-丁炔基）乙酰胺的一些尿素和2-咪唑啉酮类似物[10; 已合成[BM-5]，并测定了对分离的豚鼠回肠的毒蕈碱和抗毒蕈碱活性。发现新化合物（15-24）是毒蕈碱激动剂，部分激动剂或拮抗剂。还使用毒蕈碱拮抗剂[3H] -3-奎宁环烷基苯甲酸酯（[3H] QNB）作为配体测试了化合物与大鼠大脑皮质匀浆的体外受体结合。在此分析中发现它们的效力不及1。在豚鼠回肠上，N-3-甲基取代的咪唑烷酮类似物20是所研究的新化合物中最有效的激动剂。20在诱导回肠收缩方面的功效是5倍，对回肠毒蕈碱受体的亲和力是3-甲基取代的2-吡咯烷酮6的4倍。但是，N-3-未取代的尿素和咪唑烷酮衍生物15和19与母体乙酰胺N-甲基-N-（4-吡咯烷基-2-丁炔基）乙酰胺相比，它们的效力要低几倍[9；[UH-5]和1。部分毒蕈碱激动剂10的尿素类似
• N-methyl-N-[4-(1-pyrrolidinyl)-2-butynyl]amide congeners as muscarinic
  申请人：The United States of America as represented by the Secretary of the

  公开号：US05274121A1

  公开（公告）日：1993-12-28

  Compounds, which are muscarinic agents, having the formula ##STR1## wherein Am is --N(R).sub.a).sub.2, --N(R.sub.a).sub.3.sup.+ I.sup.-, --N (CH.sub.2).sub.n', or ##STR2## n' is an integer from 2 to 7 and R.sub.a is an alkyl having 1 to 4 carbon atoms, and each R.sub.a may be the same or different wherein the other substituents are defined hereinbelow.

  化合物是毒蕈碱类药物，其化学式为##STR1##其中Am为--N（R）.sub.a）.sub.2，--N（R.sub.a）.sub.3.sup.+ I.sup.-，--N（CH.sub.2）.sub.n'，或##STR2##n'为2至7的整数，R.sub.a为具有1至4个碳原子的烷基，且每个R.sub.a可以相同或不同，其中其他取代基在下文中定义。
• Benzothiozinone derivatives with anti-tubercular Activity−Further side chain investigation
  作者：Xiaomei Wu、Wenxin Wang、Giovanni Stelitano、Olga Riabova、Bin Wang、Wei Niu、Mario Cocorullo、Rui Shi、Laurent R. Chiarelli、Vadim Makarov、Yu Lu、Chuan Li、Chunhua Qiao

  DOI：10.1016/j.ejmech.2023.115976

  日期：2024.1

  A series of novel benzothiozinone (BTZ) derivatives were designed, prepared and evaluated for antituberculosis activity. Specifically, the BTZ pharmacophore is retained and the previous heterocyclic ring linker is replaced by alkynyl or vinyl linker, the resulting compounds displayed about 5−fold improved antimycobacterial activity. We further revealed that the linker attached tail group affects the

  设计、制备了一系列新型苯并噻嗪酮（BTZ）衍生物并评估其抗结核活性。具体而言，保留 BTZ 药效团，并用炔基或乙烯基连接基取代先前的杂环连接基，所得化合物显示出约 5 倍的抗分枝杆菌活性。我们进一步揭示，尾部连接基团会影响化合物的代谢稳定性、效力和其他药物特性。这项工作发现了两种具有可接受的低 MIC 和改善的代谢稳定性的化合物（ A1和A11 ）。代表性化合物A11在急性结核感染小鼠模型中表现出杀菌功效。
• Phenyl-substituted analogs of oxotremorine as muscarinic antagonists
  作者：Bjoern M. Nilsson、Hugo M. Vargas、Bjoern Ringdahl、Uli Hacksell

  DOI：10.1021/jm00080a013

  日期：1992.1

  A series of phenyl-substituted analogues of the muscarinic agent oxotremorine (1) have been prepared. The new compounds (3b-11b and 9c) were assayed for antimuscarinic activity on the isolated guinea pig ileum and in intact mice. They were also evaluated for ability to inhibit the binding of the muscarinic antagonist (-)-[H-3]-N-methylscopolamine to homogenates of the rat cerebral cortex. The phenyl-substituted derivatives were devoid of intrinsic muscarinic activity. Instead, they behaved as competitive muscarinic antagonists in these assays with similar or lower affinity for muscarinic receptors than the corresponding methyl-substituted analogues. The succinimide (8b) and the pyrrolidone (3b) derivatives of 1 substituted with a phenyl group at position 1 of the butynyl chain showed the highest antimuscarinic potency with dissociation constants (K(D)) of 0.10 and 0.20-mu-M, respectively, in the ileum assay. The phenyl-substituted analogues showed an approximately 10-fold lower in vivo antimuscarinic potency than their corresponding methyl-substituted positional isomers. A correlation was observed between in vitro and in vivo potency within subsets consisting of methyl- and phenyl-substituted derivatives.
• CORBEL B.; PAUGAM J.-P.; STURTZ G., CAN. J. CHEM., 1980, 58, NO 20, 2183-2188
  作者：CORBEL B.、 PAUGAM J.-P.、 STURTZ G.

  DOI：——

  日期：——