5-{5-[2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-methylisoxazole | 107355-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-{5-[2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-methylisoxazole
• 英文别名: Win 54954；5-(5-(2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxy)pentyl)-3-methylisoxazole；5-<5-(2,6-dichloro-5-oxazolylphenoxy)pentyl>-3-methylisoxazole；5-{5-[2,6-Dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxyl]-pentyl}-3-methylisoxazole；5-(5-(2,6-Dichloro-4-(4,5-Dihydro-2-Oxazoly)phenoxy)pentyl)-3-Methyl Isoxazole；5-[5-[2,6-dichloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl]-3-methyl-1,2-oxazole
• CAS: 107355-45-3
• 化学式: C₁₈H₂₀Cl₂N₂O₃
• 分子量: 383.274
• InChiKey: JJDHAOLOHQTGMG-UHFFFAOYSA-N

物化性质

• 沸点：
  555.4±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO：100 mg/mL（260.91 mM；需要超声）

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  5

制备方法与用途

WIN 54954 是一种广谱抗核糖核酸病毒药物，对人类鼻病毒、ECHO病毒9型以及肠道病毒感染均具有良好的疗效。

反应信息

• 作为产物：
  描述：

  3.5-二氯-4-羟基苯甲酸甲酯 在 氯化亚砜 、 potassium carbonate 、 sodium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 68.0h， 生成 5-{5-[2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-methylisoxazole
  参考文献：
  名称：

  一些二取代的苯基异恶唑类抗人小核糖核酸病毒的合成及结构活性研究。

  摘要：

  已经制备了广谱抗小核糖核酸病毒药物二恶草腈的许多2，6-二取代类似物，并针对几种鼻病毒血清型进行了评估。QSAR的一项研究表明，针对五种鼻病毒血清型的平均MIC（MIC）与log P密切相关。2,6-二氯类似物15在体外对MIC80为0.3 microM的鼻病毒非常有效，对几种肠病毒，并且在预防感染柯萨奇A-9的小鼠中也有效地预防了麻痹。

  DOI：

  10.1021/jm00122a027

文献信息

• Di-heterocyclic compounds and their use as antiviral agents
  申请人：Sterling Drug Inc.

  公开号：US04843087A1

  公开（公告）日：1989-06-27

  Compounds of the formulas: ##STR1## wherein Het is an oxazole or oxazine moiety; X is O, S or SO, n is an integer from 3 to 9, Y is an aliphatic bridge; and the various R groups represent hydrogen or various substituents as described herein, are useful as antiviral agents, especially against picornaviruses. N-(Chloroalkyl)amide intermediates for the compounds of Formula I are also active as antiviral agents. Related compounds outside the scope of the above formulas are also disclosed.

  公式化合物：##STR1## 其中Het是噁唑或噁唑啉基团；X是O、S或SO，n是从3到9的整数，Y是脂肪桥；各种R基团代表氢或如本文所述的各种取代基，可用作抗病毒剂，特别是对抗小RNA病毒。用于公式I化合物的N-(氯烷基)酰胺中间体也作为抗病毒剂活性。还披露了超出上述公式范围的相关化合物。
• Haloalkoxy phenyl 4,5 dihydro oxazoles
  申请人：Sterling Drug Inc.

  公开号：US04939267A1

  公开（公告）日：1990-07-03

  Compounds of the formulas: ##STR1## wherein Het is an oxazole or oxazine moiety; X is O, S or SO, n is an integer from 3 to 9, Y is an aliphatic bridge; and the various R groups represent hydrogen or various substituents as described herein, are useful as antiviral agents, especially against picornaviruses. N-(Chloroalkyl)amide intermediates for the compounds of Formula I are also active as antiviral agents. Related compounds outside the scope of the above formulas are also disclosed.

  上述公式中，化合物的公式为：##STR1## 其中Het是噁唑或噁嗪基团；X为O，S或SO，n为3至9的整数，Y为脂肪桥；各种R基团表示氢或如本文所述的各种取代基，对于抗病毒剂特别是针对小肠病毒具有用处。公式I化合物的N-(氯烷基)酰胺中间体也具有抗病毒活性。还公开了范围外的相关化合物。
• N-haloalkyl-4-(isoxazol-5-yl)alkoxy benzamides
  申请人：Sterling Drug, Inc.

  公开号：US05002960A1

  公开（公告）日：1991-03-26

  Compounds of the formulas: ##STR1## wherein Het is an oxazole or oxazine moiety; X is O, S or SO, n is an integer from 3 to 9, Y is an aliphatic bridge; and the various R groups represent hydrogen or various substituents as described herein, are useful as antiviral agents, especially against picornaviruses. N-(Chloroalkyl)amide intermediates for the compounds of Formula I are also active as antiviral agents. Related compounds outside the scope of the above formulas are also disclosed. Also disclosed are novel intermediates, N-halo-alkyl-4-(isoxazol-5-yl)alkoxybenzamides, also useful as antiviral agents.

  分子式为##STR1##的化合物，在其中Het是噁唑或噁唑烷基；X是O，S或SO，n是从3到9的整数，Y是脂肪桥；各种R基代表氢或如下所述的各种取代基，对于抗病毒剂，特别是对于小肠病毒具有用处。Formula I化合物的N-(氯代烷基)酰胺中间体也是作为抗病毒剂活性的。还披露了范围外的相关化合物。还披露了新的中间体，N-卤代烷基-4-(异噁唑-5-基)烷氧基苯甲酰胺，也可作为抗病毒剂使用。
• Isoxazole and furan derivatives, their preparation and use as antiviral agents
  申请人：STERLING WINTHROP INC.

  公开号：EP0207454A2

  公开（公告）日：1987-01-07

  Compounds of the formula are wherein: R is hydrogen or alkyl of 1 to 3 carbon atoms optionally substituted by hydroxy, lower-alkoxy, lower-alkoxyalkoxy, lower-acyloxy, halo or N=Z', wherein N=Z' is amino, lower- slkanoylamino, lower-alkylamino, di-lower-alkylamino, 1-pyrrolidyl, 1-piperidiny) or 4-morpholinyl; X is 0 or CH2; Y is an alkylene bridge of 3-9 carbon atoms, optionally interrupted by an olefinic linkage; Z is N or R5C, where R5 is hydrogen or lower-alkanoyl, with the proviso that when Z is N, R is other than hydrogen; m is 0 or 1; R, and R2 are each halogen, methyl, nitro, lower- alkoxycarbonyl or trifluoromethyl; and R3 and R4 are each hydrogen or lower-alkyl of 1-3 carbon atoms; and pharmaceutically acceptable acid-addition salts thereof, as well as methods for preparation and use thereof. The compound exhibit valuable antiviral properties.

  式中的化合物 其中 R 是氢或任选被羟基、低级烷氧基、低级烷氧基烷氧基、低级乙氧基、卤素或 N=Z' 取代的 1 至 3 个碳原子的烷基，其中 N=Z' 是氨基、低级烷酰氨基、低级烷基氨基、二低级烷基氨基、1-吡咯烷基、1-哌啶基或 4-吗啉基； X 是 0 或 CH2； Y 是 3-9 个碳原子的亚烷基桥，可选择被烯烃链节打断； Z 是 N 或 R5C，其中 R5 是氢或低级烷酰基，但当 Z 是 N 时，R 不是氢； m 为 0 或 1； R 和 R2 分别是卤素、甲基、硝基、低级烷氧羰基或三氟甲基；以及 R3 和 R4 分别是氢或 1-3 个碳原子的低级烷基；以及 其药学上可接受的酸加成盐及其制备和使用方法。这些化合物具有宝贵的抗病毒特性。
• Enteric coated soft capsules and method of preparation thereof
  申请人：STERLING WINTHROP INC.

  公开号：EP0587220A1

  公开（公告）日：1994-03-16

  Soft capsules coated with about 1 to about 20 mg/cm² of an enteric coating consisting essentially of by weight from about 60% to about 90% of a 1:1 copolymer of methacrylic acid and methyl or ethyl acrylate or methyl or ethyl methacrylate and from about 10% to about 40% of a plasticizer selected from the group consisting of triacetin, a polyethylene glycol having a molecular weight in the range from 400 to 3350, propylene glycol, dibutyl phthalate and triethyl citrate or a mixture thereof, without the need for a subcoating, and optionally additionally coated with from about 1 to about 10 mg/cm² of a protective coating consisting essentially of by weight from about 60% to about 90% of a cellulose derivative which is hydroxypropyl methylcellulose or hydroxypropyl cellulose or a mixture thereof and from about 10% to about 40% of a plasticizer selected from the group consisting of triacetin, a polyethylene glycol having a molecular weight in the range from 400 to 3350, propylene glycol, dibutyl phthalate, triethyl citrate, glycerin and diacetylated monoglycerides or a mixture thereof, and method of preparation thereof are disclosed.

  涂有约 1 至约 20 毫克/平方厘米肠溶衣的软胶囊，该肠溶衣主要由按重量计约 60% 至约 90% 的 1：甲基丙烯酸与丙烯酸甲酯或丙烯酸乙酯或甲基丙烯酸甲酯或甲基丙烯酸乙酯的 1:1 共聚物，以及约 10%至约 40%的增塑剂，增塑剂选自由三醋精、分子量在 400 至 3350 之间的聚乙二醇、丙二醇、邻苯二甲酸二丁酯和柠檬酸三乙酯或它们的混合物组成的组，无需底涂层，以及 可选择额外涂上约 1 至约 10 毫克/平方厘米的保护涂层，按重量计，保护涂层主要由约 60% 至约 90% 的纤维素衍生物（羟丙基甲基纤维素或羟丙基纤维素或它们的混合物）和约 10% 至约 40% 的增塑剂组成，增塑剂选自三醋精组、分子量在 400 至 3350 之间的聚乙二醇、丙二醇、邻苯二甲酸二丁酯、柠檬酸三乙酯、 甘油和二乙酰化单甘酯或它们的混合物、 及其制备方法。