3,5-二甲基-4-[3-(3-甲基-5-异恶唑基)丙氧基]-苯甲腈 | 130226-18-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3,5-二甲基-4-[3-(3-甲基-5-异恶唑基)丙氧基]-苯甲腈
• 中文别名: 3,5-二甲基-4-[3-(3-甲基异噁唑-5-基)丙氧基]苯腈
• 英文名称: 3,5-dimethyl-4-<<3-(3-methyl-5-isoxazolyl)propyl>oxy>benzonitrile
• 英文别名: 3,5-Dimethyl-4-[3-(3-methylisoxazol-5-yl) propyloxy]benzo-nitrile；3,5-Dimethyl-4-[3-(3-methylisoxazol-5-yl)propyloxy]benzonitrile；5-[3-(2,6-dimethyl-4-cyanophenoxy)propyl]-3-methylisoxazole；3,5-Dimethyl-4-[3-(3-methyl-1,2-oxazol-5-yl)propoxy]benzonitrile
• CAS: 130226-18-5
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: NTPDIYPZAUXUOM-UHFFFAOYSA-N

物化性质

• 熔点：
  55-57°C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二甲基-4-[3-(3-甲基-5-异恶唑基)丙氧基]-苯甲腈 以93.9的产率得到N-hydroxy-3,5-dimethyl-4-<<3-(3-methyl-5-isoxazolyl)propyl>oxy>benzenecarboxamide imine
  参考文献：
  名称：

  1,2,4-oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral

  摘要：

  式为##STR1##的化合物，其中：R.sub.1是烷基、烷氧基、羟基、环烷基、羟基烷基、烷氧基烷基或羟基烷氧基；Y是3至9个碳原子的脂肪基；R.sub.2和R.sub.3独立地是氢、烷基、烷氧基、卤素、三氟甲基和硝基；R.sub.4是烷氧基、羟基、卤代甲基、二卤代甲基、三卤代甲基、环烷基、烷氧羰基、羟基烷基、烷氧基烷基、烷基羧酸酯氧基烷基、氰基、2,2,2-三氟乙基、(4-甲基苯基)磺酰氧甲基、N.dbd.Q或CON.dbd.Q，其中N.dbd.Q是氨基、烷基氨基或二烷基氨基；或其药学上可接受的酸加成盐可用作抗病毒剂。

  公开号：

  US05349068A1
• 作为产物：
  描述：

  3,5-二甲基-4-羟基苯甲腈 、 5-(3-氯丙基)-3-甲基异噁唑 在 3,5-二甲基-4-羟基苯甲腈 作用下， 以94.1的产率得到3,5-二甲基-4-[3-(3-甲基-5-异恶唑基)丙氧基]-苯甲腈
  参考文献：
  名称：

  1,2,4-oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral

  摘要：

  式为##STR1##的化合物，其中：R.sub.1是烷基、烷氧基、羟基、环烷基、羟基烷基、烷氧基烷基或羟基烷氧基；Y是3至9个碳原子的脂肪基；R.sub.2和R.sub.3独立地是氢、烷基、烷氧基、卤素、三氟甲基和硝基；R.sub.4是烷氧基、羟基、卤代甲基、二卤代甲基、三卤代甲基、环烷基、烷氧羰基、羟基烷基、烷氧基烷基、烷基羧酸酯氧基烷基、氰基、2,2,2-三氟乙基、(4-甲基苯基)磺酰氧甲基、N.dbd.Q或CON.dbd.Q，其中N.dbd.Q是氨基、烷基氨基或二烷基氨基；或其药学上可接受的酸加成盐可用作抗病毒剂。

  公开号：

  US05349068A1

文献信息

• 1,2,4-Oxadiazolyl-phenoxyalkylisoxazoles and their use a s antiviral agents
  申请人：STERLING WINTHROP INC.

  公开号：EP0566199A1

  公开（公告）日：1993-10-20

  Compounds of the formula wherein : R1 is alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, alkoxyalkyl or hydroxyalkoxy ; Y is alkylene of 3 to 9 carbon atoms, R2 and R3 independently are hydrogen, alkyl, alkoxy, halo, trifluoromethyl or nitro ; R4 is alkoxy, hydroxy, halomethyl, dihalomethyl, trihalomethyl, cycloalkyl, alkoxycarbonyl, hydroxyalkyl, alkoxyalkyl, alkanecarbonyloxyalkyl, cyano, 2,2,2-trifluoroethyl, (4-methylphenyl)sulfonyloxymethyl, N=Q or CON=Q, where N=Q is amino, alkylamino or dialkylamino; or pharmaceutically acceptable acid-addition salts thereof are useful as antiviral agents. Preferred compounds are those wherein Y is alkylene of 3 to 5 carbon atoms and especially when R2 and R3 are in the 2- and 6- positions of the phenyl ring.

  式中的化合物 其中： R1 是烷基、烷氧基、羟基、环烷基、羟基烷基、烷氧基烷基或羟基烷氧基； Y 是 3 至 9 个碳原子的亚烷基、 R2 和 R3 分别是氢、烷基、烷氧基、卤代、三氟甲基或硝基； R4 是烷氧基、羟基、卤代甲基、二卤代甲基、三卤代甲基、环烷基、烷氧基羰基、羟基烷基、烷氧基烷基、烷羰氧基烷基、氰基、2,2,2-三氟乙基、（4-甲基苯基）磺酰氧基甲基、N=Q 或 CON=Q，其中 N=Q 是氨基、烷基氨基或二烷基氨基；或其药学上可接受的酸加成盐可用作抗病毒剂。 优选的化合物是其中 Y 为 3 至 5 个碳原子的亚烷基，特别是当 R2 和 R3 位于苯基环的 2- 和 6- 位时。
• Oxadiazoles as Ester Bioisosteric Replacements in Compounds Related to Disoxaril. Antirhinovirus Activity
  作者：Guy D. Diana、Deborah L. Volkots、Theodore J. Nitz、Thomas R. Bailey、Melody A. Long、Niranjan Vescio、Suzanne Aldous、Daniel C. Pevear、Frank J. Dutko

  DOI：10.1021/jm00041a022

  日期：1994.7

  A series of 1,2,4-oxadiazoles has been prepared as ester bioisosteres and tested against 15 human rhinovirus serotypes, and the MIC(80), the concentration which inhibits 80% or 12 of the serotypes tested, was determined. Homologation of the alkyl group attached to the oxadiazole ring resulted in a reduction in activity with increased chain length. Introduction of hydrophilic groups in this position rendered the compounds inactive. Increasing the length of the side chain attached to the isoxazole ring resulted in an increase in activity. Replacement of the methyl with alkoxyalkyl substituents retained activity; however, introduction of a hydroxyl group on to the side chain reduced activity. Compound 8a, where both the isoxazole and oxadiazole rings were substituted with methyl groups, was one of the most active compounds in the series. A comparison was made between 8a and the two isomeric oxadiazoles 41 and 46, and an attempt was made to explain the difference in activity by examining electrostatic potential maps and by an energy profiling study. No conclusive results were obtained from these studies.
• Antipicornavirus activity of tetrazole analogs related to disoxaril
  作者：Guy D. Diana、David Cutcliffe、Deborah L. Volkots、John P. Mallamo、Thomas R. Bailey、Niranjan Vescio、Richard C. Oglesby、Theodore J. Nitz、Joseph Wetzel

  DOI：10.1021/jm00074a004

  日期：1993.10

  A series of tetrazole analogues of Win 54954, a broad-spectrum antipicornavirus compound, has been synthesized to address the acid lability of the oxazoline ring of this series of compounds. The results of X-ray crystallography studies of several members of the oxazoline series bound to human rhinovirus type IA and 14 have been used to design compounds in the tetrazole series with a broad spectrum of activity. Compound 16b, which has a three-carbon linkage between the isoxazole and phenyl rings and a propyl chain extending from the isoxazole ring, exhibiting an MIC80 for 15 rhinovirus serotypes of 0.20 muM as compared to 0.40 muM for Win 54954. X-ray studies of 16b bound to human rhinovirus-14 show that the propyl side chain extends into a pore in the binding site with the possibility of hydrophobic interactions with a pocket formed by Leu106 and a portion of Ser107.
• 1,2,4-Oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral agents
  申请人：SANOFI

  公开号：EP0566199B1

  公开（公告）日：2000-03-01
• J. Med. Chem. 1995, 38, 1355-1371
  作者：

  DOI：——

  日期：——