isopropylmethylamine hydrochloride | 54565-61-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: isopropylmethylamine hydrochloride
• 英文别名: Methyl(propan-2-yl)azanium;chloride
• CAS: 54565-61-6
• 化学式: C₄H₁₁N*ClH
• 分子量: 109.599
• InChiKey: GJFBKLLFRJJEQX-UHFFFAOYSA-N

物化性质

• 溶解度：
  甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  isopropylmethylamine hydrochloride 、 1-(4-<131I>iodo-2,5-dimethoxyphenyl)-2-propanone 在 silica gel 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 1-(4-(iodo-131I)-2,5-dimethoxyphenyl)-N-isopropyl-N-methylpropan-2-amine
  参考文献：
  名称：

  Radiohalogen-labeled imaging agents. 3. Compounds for measurement of brain blood flow by emission tomography

  摘要：

  The radioiodine-labeled amines currently available as brain-imaging agents, based on our previous work and that of others, are prepared either by exchange labeling or by direct iodination of a protected intermediate. The intrinsic slowness of these processes limits their potential for use with the positron-emitting 122I, as it has a half-life of only 3.6 min. This isotope has advantages of a low dose to the patient and availability from a generator containing the parent 20-h 122Xe. To develop a radiopharmaceutical in which 122I could be utilized, we prepared a number of secondary and tertiary amines (maintaining the 2,5-dimethoxy substitution pattern which allows direct iodination at the 4-position) with 131I. The organ distributions of these compounds were studied, and the best properties were found in the N,N-dimethyl homologue (2,5-dimethoxy-N,N-dimethyl-4-iodoamphetamine). This compound was successfully synthesized in a matter of seconds, with a chemical yield and radioactive purity both in excess of 90% and an incorporation efficiency of radioiodine of about 40%.

  DOI：

  10.1021/jm00374a023
• 作为产物：
  描述：

  丙酮 、 甲胺 在 溶剂黄146 、 sodium cyanoborohydride 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 isopropylmethylamine hydrochloride
  参考文献：
  名称：

  Hit-to-Lead Optimization of a Novel Class of Potent, Broad-Spectrum Trypanosomacides

  摘要：

  The parasitic trypanosomes Trypanosoma brucei and T. cruzi are responsible for significant human suffering in the form of human African trypanosomiasis (HAT) and Chagas disease. Drugs currently available to treat these neglected diseases leave much to be desired. Herein we report optimization of a novel class of N-(2-(2-phenylthiazol-4-yl)ethyl)amides, carbamates, and ureas, which rapidly, selectively, and potently kill both species of trypanosome. The mode of action of these compounds is unknown but does not involve CYP51 inhibition. They do, however, exhibit clear structure activity relationships, consistent across both trypanosome species. Favorable physicochemical parameters place the best compounds in CNS drug-like chemical space but, as a class, they exhibit poor metabolic stability. One of the best compounds (64a) cleared all signs of T. cruzi infection in mice when CYP metabolism was inhibited, with sterile cure achieved in one mouse. This family of compounds thus shows significant promise for trypanosomiasis drug discovery.

  DOI：

  10.1021/acs.jmedchem.6b00442

文献信息

• Crowther et al., Journal of the Chemical Society, 1951, p. 1774,1778
  作者：Crowther et al.

  DOI：——

  日期：——
• WO2007/14885
  申请人：——

  公开号：——

  公开（公告）日：——
• Structure−Activity Relationships of Dimethindene Derivatives as New M₂-Selective Muscarinic Receptor Antagonists
  作者：Thomas M. Böhme、Christine Keim、Kai Kreutzmann、Matthias Linder、Theo Dingermann、Gerd Dannhardt、Ernst Mutschler、Günter Lambrecht

  DOI：10.1021/jm020895l

  日期：2003.2.1

  A series of 2,3-disubstituted indenes, which are analogues of the widely used histamine H, receptor antagonist dimethindene, have been synthesized and studied as muscarinic and histamine receptor antagonists. The affinities of these compounds for the five human muscarinic receptor subtypes (M-1-M-5) and for human histamine H, receptors were determined in radioligand binding studies using membranes from transfected Chinese hamster ovary (CHO) cells and [H-3]N-methylscopolamine ([H-3]NMS). The results demonstrate that the diisopropyl analogue 19 has a similar high affinity as (S)-dimethindene at M-2 receptors ((S)-dimethindene: pK(i) = 7.52; (-)-19: pK(i) = 7.37) with an improved selectivity pattern ((S)-dimethindene: M-2/M-1 = 6-fold, M-2/M-3 = 5-fold, M-2/M-4 = 10-fold, M-2/M-5 = 25-fold; (-)-19: M-2/M-1 = 36-fold, M-2/M-3 = 96-fold, M-2/M-4 = 42-fold, M-2/M-5 = 275-fold). In addition, compound (-)-19 showed 35-fold lower affinity at histamine H-1 receptors (pK(i) = 5.61) than (S)-dimethindene (pK(i) = 7.16). Another interesting compound is the fluoroethyl derivative 20 (pK(i)/M-2 = 7.49), which also exhibits a higher M-2 selectivity (M-2/M-1 = 19-fold; M-2/M-3 = 22-fold; M-2/M-4 = 13-fold; M-2/ M-5 = 62-fold) than (S)-dimethindene. Unfortunately, compound 20 also shows a high affinity for histamine H-1 receptors (pK(i) = 8.14). The compound with the highest affinity for M-2 receptors (pK(i) = 7.91), the dimethylaminomethylene analogue 31, displayed only a small preference for M-2 receptors. In conclusion, compound (-)-19 might be useful to test the hypothesis that blockade of muscarinic M-2 receptors in the brain is a viable mechanism by which to produce improved cognition. This second-generation dimethindene analogue might also be the starting point for the development Of M-2-selective muscarinic antagonists useful for quantifying M-2 receptors in the central nervous system with positron emission tomography imaging.
• GB922585
  申请人：——

  公开号：——

  公开（公告）日：——
• Dahl,B.M.; Nielsen,P.H., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1974, vol. 28, p. 1091 - 1095
  作者：Dahl,B.M.、Nielsen,P.H.

  DOI：——

  日期：——