2-<2-<5-(3-chloropropyl)furanyl>>-2-methyl-1,3-dioxolane | 159727-70-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-<2-<5-(3-chloropropyl)furanyl>>-2-methyl-1,3-dioxolane
• 英文别名: 2-[5-(3-chloropropyl)-2-furanyl]-2-methyl-1,3-dioxolane；2-[5-(3-Chloropropyl)furan-2-yl]-2-methyl-1,3-dioxolane
• CAS: 159727-70-5
• 化学式: C₁₁H₁₅ClO₃
• 分子量: 230.691
• InChiKey: QSAUAOBQAWSTSC-UHFFFAOYSA-N

物化性质

• 沸点：
  305.4±37.0 °C(predicted)
• 密度：
  1.171±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<2-<5-(3-chloropropyl)furanyl>>-2-methyl-1,3-dioxolane 在 氢氧化钾 、 4-甲基苯磺酸吡啶 、 potassium iodide 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 68.0h， 生成 1-<5-<3-<2,6-dimethyl-4-(5-methyl-1,2,4-oxadiazoyl)phenoxy>propyl>-2-furanyl>ethanone
  参考文献：
  名称：

  对3-甲基异恶唑的乙酰呋喃替代品的抗鼻病毒活性的评估。3-甲基异恶唑是2-乙酰基呋喃生物甾体吗？

  摘要：

  作为我们广谱抗picornaviral系列中3-甲基异恶唑部分的探针，制备了一组2-乙酰基呋喃类似物来替代3-甲基异恶唑环。两个系列的比较显示出在功效，活性谱，logP和静电参数方面的显着相似性。对与人鼻病毒14结合的21b的X射线研究表明，2-乙酰基采用了syn构象，而羰基氧则以与异恶唑的氮几乎相同的方式充当了ASN219的氢键受体。2-甲基呋喃和2-甲酰基呋喃类似物的抗病毒活性降低证实了顺式构象和氢键能力的重要性。从该研究的结果，很明显，syn-2-乙酰基呋喃环起3-甲基异恶唑的生物等排体的作用。

  DOI：

  10.1021/jm00050a014
• 作为产物：
  描述：

  2-(2-甲基[1,3]二氧戊环-2-基)呋喃 、 1-溴-3-氯丙烷 在 叔丁基锂 作用下， 生成 2-<2-<5-(3-chloropropyl)furanyl>>-2-methyl-1,3-dioxolane
  参考文献：
  名称：

  对3-甲基异恶唑的乙酰呋喃替代品的抗鼻病毒活性的评估。3-甲基异恶唑是2-乙酰基呋喃生物甾体吗？

  摘要：

  作为我们广谱抗picornaviral系列中3-甲基异恶唑部分的探针，制备了一组2-乙酰基呋喃类似物来替代3-甲基异恶唑环。两个系列的比较显示出在功效，活性谱，logP和静电参数方面的显着相似性。对与人鼻病毒14结合的21b的X射线研究表明，2-乙酰基采用了syn构象，而羰基氧则以与异恶唑的氮几乎相同的方式充当了ASN219的氢键受体。2-甲基呋喃和2-甲酰基呋喃类似物的抗病毒活性降低证实了顺式构象和氢键能力的重要性。从该研究的结果，很明显，syn-2-乙酰基呋喃环起3-甲基异恶唑的生物等排体的作用。

  DOI：

  10.1021/jm00050a014

文献信息

• Therapeutic phenoxyalklpyridazines and intermediates therefor
  申请人：Sterling Winthrop Inc.

  公开号：US05514679A1

  公开（公告）日：1996-05-07

  Compounds of the formula ##STR1## wherein: R.sub.1 and R.sub.2 are independently hydrogen, halo, alkyl, alkenyl, alkoxy, hydroxy, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, alkylthioalkynyl, hydroxyalkoxy, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, amino, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy or cyanomethyl, nitro, difluoromethyl, trifluoromethyl or cyano; Y is alkylene of 3 to 9 carbon atoms; R.sub.3 and R.sub.4 are independently hydrogen, alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkanoyl, alkanoyloxy, alkylsulfinylalkyl, alkylsulfonylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy, cyanomethyl, fluoroalkyl, cyano, phenyl, alkynyl, alkene, or halo; R.sub.5 is alkoxycarbonyl, alkyltetrazolyl, phenyl or a heterocycle; or a pharmaceutically acceptable acid addition salts thereof; N-oxides thereof, are useful as antipirconaviral agents.

  式为##STR1##的化合物，其中：R.sub.1和R.sub.2独立地是氢、卤素、烷基、烯基、烷氧基、羟基、羟基烷基、羟基卤代烷基、烷氧基烷基、烷硫烯基、羟基烷氧基、烷硫基烷基、烷基磺酰基烷基、烷基磺基烷基、氨基、氨基烷基、烷基氨基烷基、二烷基氨基烷基、烷氧羰基、羧基或氰甲基、硝基、二氟甲基、三氟甲基或氰基；Y为3至9个碳原子的烷基；R.sub.3和R.sub.4独立地是氢、烷基、烷氧基、羟基、环烷基、羟基烷基、羟基卤代烷基、烷氧基烷基、羟基烷氧基、烷硫基烷基、烷酰基、烷酰氧基、烷基磺酰基烷基、烷基磺基烷基、氨基烷基、烷基氨基烷基、二烷基氨基烷基、烷氧羰基、羧基、氰甲基、氟烷基、氰基、苯基、炔基、烯烃或卤素；R.sub.5为烷氧羰基、烷基四唑基、苯基或杂环；或其药学上可接受的酸盐；其N-氧化物可用作抗逆转录病毒药物。
• Picornavirus Inhibitors: Trifluoromethyl Substitution Provides a Global Protective Effect against Hepatic Metabolism
  作者：Guy D. Diana、Patrick Rudewicz、Daniel C. Pevear、Theodore J. Nitz、Suzanne C. Aldous、David J. Aldous、David T. Robinson、Tandy Draper、Frank J. Dutko、Christopher Aldi、Guy Gendron、R. Christopher Oglesby、Deborah L. Volkots、Michael Reuman、Thomas R. Bailey、Richard Czerniak、Tracey Block、Robert Roland、James Oppermann

  DOI：10.1021/jm00008a014

  日期：1995.4.1

  Several modifications of the oxazoline ring of WIN 54954, a broad spectrum antipicornavirus compound, have been prepared in order to address the acid lability and metabolic instability of this compound. We have previously shown that the oxadiazole analogue 3 displayed comparable activity against a variety of rhinoviruses and appeared to be stable to acid. A monkey liver microsomal assay was developed to examine the metabolic stability in vitro of both compounds, and it was determined that WIN 54954 displayed 18 metabolic products while 3 was converted to 8 products. Two major products of 3 were determined by LC-MS/MS to be monohydroxylated at each of the terminal methyl groups. Replacement of the methyl on the isoxazole ring with a trifluoromethyl group, while preventing hydroxylation at this position, did not reduce the sensitivity of the molecule to microsomal metabolism at other sites. However, the (trifluoromethyl)oxadiazole 9 not only prevented hydroxylation at this position but also provided protection at the isoxazole end of the molecule, resulting in only two minor products to the extent of 4%. The major product was identified as the monohydroxylated compound 23. The global metabolic protective effect of trifluoromethyl group on the oxadiazole ring was further demonstrated by examining a variety of analogues including heterocyclic replacements of the isoxazole ring. In each case, the trifluoromethyl analogue displayed a protective effect when compared to the corresponding methyl analogue.
• US5514679A
  申请人：——

  公开号：US5514679A

  公开（公告）日：1996-05-07
• US5567717A
  申请人：——

  公开号：US5567717A

  公开（公告）日：1996-10-22
• US5665763A
  申请人：——

  公开号：US5665763A

  公开（公告）日：1997-09-09