3-甲基氨基-1-丁炔 | 4070-90-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-甲基氨基-1-丁炔
• 英文名称: N-methyl-N-(1-methyl-prop-2-inyl)-amine
• 英文别名: N-methyl-N-(1-methyl-2-propynyl)amine；(+/-)-N-methyl-3-butyn-2-amine；3-(methylamino)but-1-yne；N-methylbut-3-yn-2-amine；N-methyl-2-amino-3-butyne；3-methylamino-1-butyne
• CAS: 4070-90-0
• 化学式: C₅H₉N
• mdl: MFCD00041666
• 分子量: 83.1332
• InChiKey: SEDYEJKMKNWLGX-UHFFFAOYSA-N

物化性质

• 沸点：
  88 °C(Press: 740 Torr)
• 密度：
  0.799±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2921199090

反应信息

• 作为反应物：
  描述：

  3-甲基氨基-1-丁炔 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 R-(+)-N<3-(2,4-dichlorophenoxy)propyl>-N-methyl-3-butyn-2-amine
  参考文献：
  名称：

  Inhibition of monoamine oxidase by the R and S enantiomers of N[3-(2,4-dichlorophenoxy)propyl]-N-methyl-3-butyn-2-amine

  摘要：

  The chemical synthesis of the R-(+)- and S-(-)-enantiomers of N[3-(2,4-dichlorophenoxy)propyl]-N-methyl-3-butyn-2-amine is described. These compounds are derivatives of the mechanism-based irreversible monoamine oxidase inhibitor clorgyline in which a methyl group is substituted for a hydrogen atom on the propargyl methylene carbon. The enantiomeric clorgyline derivatives were both found to be reversible, linearly-competitive inhibitors of monoamine oxidase-A and -B. Thus the methyl-substitution does not prevent non-covalent binding of the inhibitors to the active sites, but it does prevent these compounds from reacting within that complex to form covalent adducts with the enzymes. The substitution of the methyl group resulted in a decreased affinity, as compared to clorgyline, for non-covalent binding to monoamine oxidase-A, with the S-enantiomer having the lower affinity. In contrast, the S-enantiomer showed increased affinity for monoamine oxidase-B. These effects resulted in the high selectivity of the parent compound, clorgyline, towards monoamine oxidase-A being lost. The R-enantiomer showed a small degree of selectivity towards the A-form of the enzyme, whereas the S-enantiomer had a higher affinity for the B-form. These results are discussed in terms of the chemical mechanisms proposed for the interactions of the monoamine oxidases with substrates and inhibitors.

  DOI：

  10.1016/0223-5234(92)90059-a
• 作为产物：
  描述：

  (R)-(+)-3-丁炔-2-醇 、 甲胺 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 3-甲基氨基-1-丁炔
  参考文献：
  名称：

  [EN] NEW ARYLALKENYLPROPARGYLAMINE DERIVATIVES EXHIBITING NEUROPROTECTIVE ACTION FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
  [FR] NOUVEAUX DÉRIVÉS ARYLALCÉNYLPROPARGYLAMINE FAISANT PREUVE D'ACTION NEUROPROTECTRICE POUR LE TRAITEMENT DES MALADIES NEURODÉGÉNÉRATIVES

  摘要：

  本发明涉及一类新型的芳基烯丙炔丙胺衍生物，其具有通用公式（I）或其对应的手性异构体或对映异构体或盐，可选用药物上可接受的盐，或者这些化合物的溶剂化物。这些化合物可用于治疗或预防哺乳动物与单胺氧化酶功能障碍相关的疾病或状况，特别是在神经退行性疾病中，例如帕金森病、阿尔茨海默病或亨廷顿病。

  公开号：

  WO2015087094A1

文献信息

• Propargyl-trifluoromethoxy-amino-benzothiazole derivatives
  申请人：——

  公开号：US20040176430A1

  公开（公告）日：2004-09-09

  The subject invention provides compounds having the structure: 1 wherein R 1 is present or absent, and when present is H, C 1 -C 6 alkyl, C 1 -C 6 alkynyl, —(CH 2 ) y S(CH 2 ) x CH 3 , C 1 -C 6 aminoalkyl, C 1 -C 6 hydroxyalkyl or —(CH 2 ) n C(═O)(C 6 H 4 )(CH 2 )R 2 ; R 2 is H or C 1 -C 4 alkyl; R 3 is H or C 1 -C 4 alkyl; R 4 is present or absent, and when present is H, C 1 -C 6 alkyl, C 1 -C 6 alkynyl, —(CH 2 ) y S(CH 2 ) x CH 3 , C 1 -C 6 aminoalkyl, C 1 -C 6 hydroxyalkyl or —(CH 2 ) n C(═O)(C 6 H 4 )(CH 2 )R 2 ; wherein n is an integer from 1-6; wherein x is 0 or an integer from 1-5 and y is an integer from 1-5, such that x+y<6; at least one of R 1 or R 4 is present; the dashed line represents a bond between one of the nitrogen atoms and the intervening carbon atom; and any compound is charged when both R 1 and R 4 are present, or any specific enantiomer thereof or any pharmaceutically acceptable salt thereof, and a method for treating a neurologic disorder or multiple sclerosis by administering a therapeutically effective amount any of the compounds.

  本发明提供具有以下结构的化合物： 其中R1存在或不存在，当存在时为H、C1-C6烷基、C1-C6炔基、—(CH2)yS(CH2)xCH3、C1-C6氨基烷基、C1-C6羟基烷基或—(CH2)nC(═O)(C6H4)(CH2)R2；R2为H或C1-C4烷基；R3为H或C1-C4烷基；R4存在或不存在，当存在时为H、C1-C6烷基、C1-C6炔基、—(CH2)yS(CH2)xCH3、C1-C6氨基烷基、C1-C6羟基烷基或—(CH2)nC(═O)(C6H4)(CH2)R2；其中n为1-6的整数；其中x为0或1-5的整数，y为1-5的整数，使得x+y<6；R1或R4中至少有一个存在；虚线表示氮原子和介入碳原子之间的键；当R1和R4同时存在时，任何化合物都带电，或其任何特定对映体或其任何药用盐，以及通过给予任何化合物的治疗有效量来治疗神经系统疾病或多发性硬化的方法。
• Novel Arylalkenylpropargylamines as Neuroprotective, Potent, and Selective Monoamine Oxidase B Inhibitors for the Treatment of Parkinson’s Disease
  作者：Paul B. Huleatt、Mui Ling Khoo、Yi Yuan Chua、Tiong Wei Tan、Rou Shen Liew、Balázs Balogh、Ruth Deme、Flóra Gölöncsér、Kalman Magyar、David P. Sheela、Han Kiat Ho、Beáta Sperlágh、Péter Mátyus、Christina L. L. Chai

  DOI：10.1021/jm501722s

  日期：2015.2.12

  To develop novel neuroprotective agents, a library of novel arylalkenylpropargylamines was synthesized and tested for inhibitory activities against monoamine oxidases. From this, a number of highly potent and selective monoamine oxidase B inhibitors were identified. Selected compounds were also tested for neuroprotection in in vitro studies with PC-12 cells treated with 6-OHDA and rotenone, respectively

  为了开发新型神经保护剂，合成了新型芳基烯基炔丙基胺的文库，并测试了其对单胺氧化酶的抑制活性。由此，鉴定出许多高效且选择性的单胺氧化酶B抑制剂。在体外研究中，还分别用6-OHDA和鱼藤酮处理过的PC-12细胞测试了所选化合物的神经保护作用。观察到一些测试的化合物在用神经毒素处理过的PC-12细胞中存活率显着提高。这表明这些炔丙基胺能够赋予针对毒素作用的保护作用，并且还可以被认为是新型疾病缓解帕金森氏病的药物，这是治疗帕金森氏病非常需要的药物。
• DE1946112
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2008/101682
  申请人：——

  公开号：——

  公开（公告）日：——
• FR2272983
  申请人：——

  公开号：——

  公开（公告）日：——