6-(1,3-噻唑烷-3-基)己烷-1-胺 | 88346-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 6-(1,3-噻唑烷-3-基)己烷-1-胺
• 英文名称: 3-(6-aminohexyl)-1,3-thiazolidine
• 英文别名: 6-(1,3-Thiazolidin-3-yl)hexan-1-amine
• CAS: 88346-63-8
• 化学式: C₉H₂₀N₂S
• 分子量: 188.337
• InChiKey: YUOQBWWXBSRINF-UHFFFAOYSA-N

物化性质

• 沸点：
  150 °C(Press: 0.3 Torr)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(1,3-噻唑烷-3-基)己烷-1-胺 在 lithium aluminium tetrahydride 、 碘 、 三乙胺 、 potassium iodide 作用下， 以 1,4-二氧六环 、 乙醇 、 苯 为溶剂， 反应 22.0h， 生成 N,N'-bis<6-<(o-aminobenzyl)amino>hexyl>cystamine
  参考文献：
  名称：

  1,2,3,4-四氢喹唑啉衍生物的合成作为潜在的α-肾上腺素能阻断剂

  摘要：

  合成N，N- ' -双[6-（1,2,3,4-四氢-3- quinazolidyl）己基]胱胺（I）和3-（6-氨基己基）-1,2,3,4-描述了四氢喹唑啉（II）。通过使邻硝基苯甲酰氯与3-（6-氨基己基）-1，3-噻唑烷（III）缩合，然后二聚，还原并形成四氢喹唑啉环，来获得化合物I。类似的方法用于制备化合物II。这些化合物和某些合成中间体是潜在的α-肾上腺素能阻滞剂。

  DOI：

  10.1002/jhet.5570200525
• 作为产物：
  描述：

  1,6-己二胺 、 环硫乙烷 、 sodium formaldehyde bisulfite 以53%的产率得到
  参考文献：
  名称：

  GRANADOS, R.;ALVAREZ, M.;VALLS, N.;SALAS, M., J. HETEROCYCL. CHEM., 1983, 20, N 5, 1271-1275

  摘要：

  DOI：

文献信息

• Synthesis of 2-hydroxy-2-phenylethylamino derivatives as potential α-adrenergic blocking agents
  作者：M. Alvarez、R. Granados、R. Lavilla、M. Salas

  DOI：10.1002/jhet.5570220326

  日期：1985.5

  synthesis of N,N'-bis[6-(2-hydroxy-2-phenylethylamino)hexyl] cystamines 4, and N-(2-hydroxy-2-phenylethyl)-1,6-hexanediamines 6 are described. Compounds 4 were obtained by condensation of the requisite epoxide 2 with 3-(6-aminohexyl)-1,3-thiazolidine followed by dimerization with opening of the thiazolidine ring. A similar method was used for the preparation of compounds 6. In order to prepare 4j (N,N'-bis6-[2-hydroxy-2(3

  合成N，N'-双[6-（2-羟基-2-苯乙氨基）己基] cystamines 4，和N-（2-羟基-2-苯乙基）-1,6- hexanediamines 6中描述。通过将必需的环氧化物2与3-（6-氨基己基）-1，3-噻唑烷缩合，然后通过打开噻唑烷环进行二聚来获得化合物4。用类似的方法制备化合物6。为了制备4j（N，N′-双6- [2-羟基-2（3，4-二羟基苯基）乙基氨基]己基}胱胺），有几种方法。经过测试 选择的方法涉及使用两个羟基都被保护为甲氧基甲基醚的3，4-二羟基苯甲醛。
• Structure-activity relationships among di- and tetramine disulfides related to benextramine
  作者：M. Alvarez、R. Granados、D. Mauleon、G. Rosell、M. Salas、J. Salles、N. Valls

  DOI：10.1021/jm00390a011

  日期：1987.7

  The synthesis and irreversible alpha-blocking activity in the rat vas deferens of a series of tetra- and diamine disulfides 2-38, structural analogues of benextramine (BHC), are described. All compounds containing a central cystamine moiety displayed an irreversible alpha-adrenergic blockade at concentrations ranging from 10(-4) to 6 X 10(-6)M. Potency was increased in cystamines N,N'-disubstituted with 6-aminohexyl groups, especially when the outer nitrogen atoms bear arylalkyl substituents or are enclosed in a ring. However, N,N,N',N'-tetrasubstituted cystamines were poor blockers. Structural specificity in the outer portion of the tetramine disulfide is low, since many types of substituents gave rise to potent alpha-blockers. Even replacement of the outer amines with nonbasic ethers or amides was observed to maintain irreversible alpha-blockade.
• Structure-activity relationships among benextramine-related tetraamine disulfides. Chain length effect on .alpha.-adrenoreceptor blocking activity
  作者：Wilma Quaglia、Livio Brasili、Gloria Cristalli、Dario Giardina、Maria T. Picchio、Carlo Melchiorre

  DOI：10.1021/jm00117a030

  日期：1988.9

  Several N'-substituted N,N''-(dithiodi-2,1-ethanediyl)bis(1, omega-alkanediamines) were prepared and evaluated for their blocking activity on alpha-adrenoreceptors in the isolated rat vas deferens and human blood platelets. The results were compared with those obtained for benextramine (N,N''-(dithiodi-2,1-ethanediyl)bis[N'-[(2-methoxyphenyl)-methyl]- 1 ,6- hexanediamine], 10). Bendotramine (N,N''-(dithiodi-2,1-ethanediyl)bis[N'-[(2-methoxyphenyl)- methyl]-1,12-dodecanediamine], 16) proved to be as active as 10 on alpha 1-adrenoreceptors, showing that optimum activity is associated with two carbon chain lengths separating inner from outer nitrogens of tetraamine disulfides. On the other hand, 16 had no activity up to 20 microM at alpha 2-adrenoreceptors. The optimum activity at this receptor subtype was associated with a six to eight carbon chain (10-12). Furthermore, 10 proved to be more selective toward alpha 2-adrenoreceptors whereas 16 was a selective alpha 1-antagonist. The tetraamine disulfides were shown also to be potent inhibitors of human platelet aggregation induced by ADP or epinephrine. The potency increased with the carbon chain length. However, the results on platelets did not parallel those found in the rat vas deferens, indicating that differences exist between the alpha-adrenoreceptor subtypes investigated. In conclusion, 10 may be a useful tool in characterizing alpha 2-adrenoreceptors whereas 16 might help in investigating alpha 1-adrenoreceptors.
• Melchiorre; Gulini; Giardina, European Journal of Medicinal Chemistry, 1984, vol. 19, # 1, p. 37 - 42
  作者：Melchiorre、Gulini、Giardina、et al.

  DOI：——

  日期：——
• Synthesis and α1-antagonist activity of new prazosin- and benextramine-related tetraamine disulfides
  作者：D Giardinà、M Crucianelli、U Gulini、G Marucci、C Melchiorre、S Spampinato

  DOI：10.1016/s0223-5234(97)84357-7

  日期：1997.1

  Tetraamine disulfides 1-10 were designed by combining the structural features of benextramine, an irreversible alpha(1)/alpha(2)-adrenoceptor antagonist, and prazosin, a selective competitive alpha(1)-antagonist. Their biological profile was assessed by functional and binding assays. In rat vas deferens functional experiments, tetraamine disulfides 1-10 displayed a marked selectivity at alpha(1)-adrenoceptors. Furthermore, they acted as competitive antagonists at alpha(1)-adrenoceptors and weak noncompetitive (irreversible) antagonists at alpha(2)-adrenoceptors. In binding assays, performed at alpha(1)-adrenoceptors of rat liver (alpha 1B) and submaxillary gland (alpha(1A), compound 5 showed an 11-fold selectivity for alpha(1B)-adrenoceptors in contrast to both prazosin and benextramine, which were not selective or selective for the alpha(1A)-subtype respectively.