1-methyl-4-(3'-phenyl-3'-hydroxypropyl)piperazine | 60867-91-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-methyl-4-(3'-phenyl-3'-hydroxypropyl)piperazine
• 英文别名: 3-(4-methylpiperazin-1-yl)-1-phenylpropan-1-ol；3-(4-Methylpiperazino)-1-phenylpropanol；3-(4-Methyl-1-piperazinyl)-1-phenyl-1-propanol
• CAS: 60867-91-6
• 化学式: C₁₄H₂₂N₂O
• 分子量: 234.341
• InChiKey: NWZJYCPAZYGHLT-UHFFFAOYSA-N

物化性质

• 沸点：
  362.3±42.0 °C(Predicted)
• 密度：
  1.057±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-4-(3'-phenyl-3'-hydroxypropyl)piperazine 生成 3-(4-Methylpiperazino)-1-phenylpropyl Chloride
  参考文献：
  名称：

  PROTIVA, M.;VALENTA, V.

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯-1-苯基丙醇 在 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 52.0h， 生成 1-methyl-4-(3'-phenyl-3'-hydroxypropyl)piperazine
  参考文献：
  名称：

  Simplified Heterocyclic Analogues of Fluoxetine Inhibit Inducible Nitric Oxide Production in Lipopolysaccharide-Induced BV2 Cells

  摘要：

  合成了一系列氟西汀，替换并简化了N-甲基氨基团，并测试了它们对脂多糖（LPS）诱导的BV2细胞中一氧化氮（NO）产生和诱导性NO合酶（iNOS）表达的抑制作用。尽管合成的化合物一般显示出比氟西汀弱的活性或更大的细胞毒性，但化合物10a中氟西汀的N-甲基氨基团被莫尔夫啉替换，且三氟甲基苯环被简单的氧基取代，在10、20和40μM浓度下以剂量依赖的方式抑制了NO的产生，且其细胞毒性低于氟西汀，在同样浓度下抑制了LPS诱导的BV2细胞中的iNOS mRNA和蛋白表达。结果表明，氟西汀中的三氟甲基苯环结构对于抑制NO产生并不是必需的，且10a具备作为NO产生强效抑制剂的潜力。

  DOI：

  10.1248/bpb.34.538

文献信息

• Propanolamine derivatives, their preparation and use
  申请人：NOVO NORDISK A/S

  公开号：EP0576766A1

  公开（公告）日：1994-01-05

  Compounds of formula I wherein X is phenyl unsubstituted or optionally substituted with one or more cyano, halogeno, halogenoalkyl, C1-6-alkoxy, C1-6-alkyl, C1-5-alkanoyl, C3-5-alkenyl, aryloxy, aralkoxy, amino, C1-6-alkyl mono or disubstituted amino, C1-4-alkanoylamino, carbamoyl, C1-4-alkyl N-mono or disubstituted carbamoyl, C1-4-alkyl substituted with amino, C1-2-alkyl mono or disubstituted amino, N0₂, morpholino or imidazolyl; and R is 3,4-methylenedioxyphenyl, aryl or heteroaryl all of which can be optionally substituted with one or more cyano, halogeno, C1-6-alkyl, C1-6-alkoxy, C2-6-alkenyl, trifluoromethyl, C3-5-alkylene, aryloxy, aralkoxy or C1-6-alkylthio; and R¹ and R² are C1-10-alkyl, C3-7-cycloalkyl, C2-10-alkenyl, C3-6-cycloalkyl-C1-5-alkyl, all of which can be unsubstituted or substituted with C1-5-alkyl, C1-5-alkoxy or cyano; or R¹ and R² together form a 5, 6 or 7 membered ring containing at least one nitrogen atom, or which optionally contains two nitrogen atoms, one or two oxygen atom(s) or one or two sulphur atom(s) or a combination thereof, which ring is unsubstituted or optionally substituted with C1-4-alkyl, C1-4-alkoxy or aryl; and R³, R⁴, R⁵, R⁶, and R⁷ independently are hydrogen, C1-4-alkyl or phenyl; or R⁴ and X together form a carbocyclic ring containing 5 or 6 atoms, or a salt thereof with a pharmaceutically acceptable acid; provided however that R¹ and R² are not C3-7-cycloalkyl, C1-10-alkyl or C2-10-alkenyl which may be straight, branched or cyclic, unsubstituted or substituted with C1-4-alkoxy, aryloxy or cycloalkyl, cyano or cycloalkylalkyl, when X is phenyl substituted with cyano, halogen, halogenalkyl, C1-6-alkoxy, C1-6-alkyl, C1-5-alkanoyl, C3-5-alkylene, aryloxy or aralkoxy, are useful in the treatment of anoxia, traumatic injury, ischemia, migraine, epilepsy, Parkinson's disease, Alzheimer's disease and other neurodegenerative diseases.

  化合物的公式I，其中X是苯基，未取代或可选地取代一个或多个氰基，卤基，卤代烷基，C1-6-烷氧基，C1-6-烷基，C1-5-酰基，C3-5-烯基，芳氧基，芳基氧基，氨基，C1-6-烷基单取代或双取代氨基，C1-4-酰胺基，氨基甲酰基，C1-4-烷基N-单取代或双取代的氨基甲酰基，C1-4-烷基取代氨基，C1-2-烷基单取代或双取代氨基，N0₂，吗啉基或咪唑基；以及R是3,4-亚甲二氧基苯基，芳基或杂环芳基，所有这些都可以可选地取代一个或多个氰基，卤基，C1-6-烷基，C1-6-烷氧基，C2-6-烯基，三氟甲基，C3-5-亚烷基，芳基氧基，芳基氧基或C1-6-烷硫基；以及R¹和R²是C1-10-烷基，C3-7-环烷基，C2-10-烯基，C3-6-环烷基-C1-5-烷基，所有这些都可以未取代或取代C1-5-烷基，C1-5-烷氧基或氰基；或R¹和R²一起形成一个含有至少一个氮原子的5、6或7元环，或可选地含有两个氮原子，一个或两个氧原子或一个或两个硫原子或其组合，该环未取代或可选地取代C1-4-烷基，C1-4-烷氧基或芳基；以及R³、R⁴、R⁵、R⁶和R⁷分别是氢，C1-4-烷基或苯基；或者R⁴和X一起形成一个含有5或6个原子的碳环，或其与药学上可接受的酸的盐；但是，当X是取代有氰基，卤基，卤代烷基，C1-6-烷氧基，C1-6-烷基，C1-5-酰基，C3-5-亚烷基，芳氧基或芳基氧基时，R¹和R²不是C3-7-环烷基，C1-10-烷基或C2-10-烯基，可以是直链，支链或环状，未取代或取代有C1-4-烷氧基，芳氧基或环烷基，氰基或环烷基烷基。这些化合物在缺氧，创伤性损伤，缺血，偏头痛，癫痫，帕金森病，阿尔茨海默病和其他神经退行性疾病的治疗中是有用的。
• Synthesis of benzenepropanamine analogues as non-detergent spermicides with antitrichomonas and anticandida activities
  作者：S.T.V.S. Kiran Kumar、Vishnu Lal Sharma、Manish Kumar、Praveen Kumar Shukla、Pratibha Tiwari、Rajeev Kumar Jain、Jagdamba Prasad Maikhuri、Divya Singh、Gopal Gupta、Man Mohan Singh

  DOI：10.1016/j.bmc.2006.06.003

  日期：2006.10

  Fifteen analogues of benzenepropanamine were synthesized and evaluated for their spermicidal as well as microbicidal activities against Trichomonas vaginalis and Candida spp. Several compounds showed appreciable dual activities. Compound 12 exhibited good spermicidal (MEC = 0.1%) along with substantial anticandidal (MIC = 0.05%) activities, while compounds 3 and 6 showed significant microbicidal activities with moderate spermicidal effect. The SAR of these structures is being discussed here in this communication. It is concluded that suitable structural modifications in this class of compounds at 3-amino position may lead to a potent spermicide with associated microbicidal activity. (c) 2006 Elsevier Ltd. All rights reserved.
• Valenta, Vladimir; Bartosova, Marie; Protiva, Miroslav, Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 5, p. 1280 - 1287
  作者：Valenta, Vladimir、Bartosova, Marie、Protiva, Miroslav

  DOI：——

  日期：——
• VALENTA V.; BARTOSOVA M.; PROTIVA M., COLLECT. CZECH. CHEM. COMMUN., 1981, 46, NO 5, 1280-1287
  作者：VALENTA V.、 BARTOSOVA M.、 PROTIVA M.

  DOI：——

  日期：——
• PROTIVA, M.;VALENTA, V.
  作者：PROTIVA, M.、VALENTA, V.

  DOI：——

  日期：——