5-(4-fluorophenoxy)furan-2-carboxaldehyde | 141580-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-fluorophenoxy)furan-2-carboxaldehyde
• 英文别名: 5-(4-fluorophenoxy)-2-furancarbaldehyde；5-(4-fluorophenoxy)-2-furfuraldehyde；5-(4-fluoro-phenoxy)-furan-2-carbaldehyde；5-(4-fluorophenoxy)-2-furaldehyde；5-(4-Fluorophenoxy)furan-2-carbaldehyde
• CAS: 141580-53-2
• 化学式: C₁₁H₇FO₃
• 分子量: 206.173
• InChiKey: CFKRLHFQRLBKSK-UHFFFAOYSA-N

物化性质

• 沸点：
  326.6±32.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-fluorophenoxy)furan-2-carboxaldehyde 在 双(乙腈)氯化钯(II) 、 sodium hydroxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 copper(l) iodide 、 碘 、 二异丙胺 、 三苯基膦 、 potassium iodide 作用下， 以 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 3.5h， 生成 (3R)-5-[5-(4-fluorophenoxy)furan-2-yl]-3-methyl-3H-1,2-oxazole-2-carboxamide
  参考文献：
  名称：

  Synthesis of A-79175: a second generation 5-lipoxygenase inhibitor

  摘要：

  A convergent, high yielding, and scalable synthesis of A-79175, with a key step involving a mild and efficient Cu-Pd catalyzed coupling reaction of a terminal acetylene with a substituted 2-iodofuran is discussed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00159-6
• 作为产物：
  描述：

  4-氟苯酚 、 5-硝基糠醛二乙酸酯 在 potassium tert-butylate 作用下， 生成 5-(4-fluorophenoxy)furan-2-carboxaldehyde
  参考文献：
  名称：

  Synthesis of A-79175: a second generation 5-lipoxygenase inhibitor

  摘要：

  A convergent, high yielding, and scalable synthesis of A-79175, with a key step involving a mild and efficient Cu-Pd catalyzed coupling reaction of a terminal acetylene with a substituted 2-iodofuran is discussed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00159-6

文献信息

• Acetylene derivatives having lipoxygenase inhibitory activity
  申请人：Abbott Laboratories

  公开号：US05476873A1

  公开（公告）日：1995-12-19

  Compounds of the structure ##STR1## where p and q are zero or one, but cannot both be the same, M is a pharmaceutically acceptable cation or a metabolically cleavable group, B is a valence bond or a straight or branched alkylene group, R is alkyl, cycloalkyl or --NR.sup.1 R.sup.2, where R.sup.1 and R.sup.2 are hydrogen, alkyl, cycloalkyl or alkanoyl, and A is optionally substituted carbocyclic aryl, furyl, benzo[b]furyl, thienyl, or benzo[b]thienyl are potent inhibitors of lipoxygenase enzymes and thus inhibit the biosynthesis of leukotrienes. These compounds are useful in the treatment or amelioration of allergic and inflammatory disease states.

  结构为##STR1##的化合物，其中p和q为零或一，但不能同时相同，M是一种药用可接受的阳离子或代谢可裂解基团，B是一个价键或直链或支链烷基基团，R是烷基、环烷基或--NR.sup.1 R.sup.2，其中R.sup.1和R.sup.2是氢、烷基、环烷基或烷酰基，A是可选择取代的碳环芳基、呋喃基、苯并[b]呋喃基、噻吩基或苯并[b]噻吩基，是脂氧合酶酶的强效抑制剂，从而抑制白三烯的生物合成。这些化合物在治疗或缓解过敏和炎症性疾病状态中很有用。
• Lipoxygenase and cyclooxygenase inhibiting compounds
  申请人：Abbott Laboratories

  公开号：US05516789A1

  公开（公告）日：1996-05-14

  Compounds having the structure ##STR1## or a pharmaceutically acceptable salt thereof have activity as inhibitors of cylooxygenase and 5-lipoxygenase, reduce the biosynthesis of leukotrienes B.sub.4, C.sub.4, D.sub.4, and E.sub.4 and cylooxygenase products such as prostaglandins and thromboxane and are useful in the treatment of inflammatory and allergic disease states. The compounds have the structure indicated above wherein A is selected from (a) optinally substituted carbocyclic aryl, (b) optinally substituted furyl, (c) optinally substituted benzo[b]furyl, (d) optinally substituted thienyl, (e) optinally substituted pyridyloxy, (f) optinally substituted pyridylalkyl, (g) optinally substituted benzo[b]thienyl, (h) optinally substituted pyridyl, (i) optinally substituted quinolyl, and (j) optinally substituted indolyl; X is selected from (a) optionally substituted alkyl, (b) optinally substituted alkenyl, and (c) optinally substituted alkynyl; R.sup.1 and R.sup.2 are independently selected from hydrogen, hydroxy, and alkyl; and Z is a residue of a non-steroidal anti-inflammatory drug of the general formula Z--COOH.

  具有上述结构##STR1##或其药用可接受盐的化合物具有作为环氧合酶和5-脂氧合酶的抑制剂的活性，可减少白三烯B.sub.4、C.sub.4、D.sub.4和E.sub.4以及环氧合酶产物如前列腺素和血栓素的生物合成，并可用于治疗炎症和过敏疾病状态。这些化合物具有上述指示的结构，其中A选自(a)可选择地取代的碳环芳基、(b)可选择地取代的呋喃基、(c)可选择地取代的苯并[b]呋喃基、(d)可选择地取代的噻吩基、(e)可选择地取代的吡啶氧基、(f)可选择地取代的吡啶基烷基、(g)可选择地取代的苯并[b]噻吩基、(h)可选择地取代的吡啶基、(i)可选择地取代的喹啉基，和(j)可选择地取代的吲哚基；X选自(a)可选择地取代的烷基、(b)可选择地取代的烯基，和(c)可选择地取代的炔基；R.sup.1和R.sup.2各自选自氢、羟基和烷基；Z是一种非类固醇抗炎药的一般公式Z--COOH的残基。
• Thienithiazine derivatives
  申请人：Chemisch Pharmazeutische Forschungsgesellschaft m.b.H.

  公开号：US05679678A1

  公开（公告）日：1997-10-21

  Thienothiazine derivatives of the formula ##STR1## are provided. These derivatives are useful for the treatment of inflammation and pain.

  提供了公式为##STR1##的噻唑啉衍生物。这些衍生物可用于治疗炎症和疼痛。
• N-substituted-furylalkenyl hydroxamic acid and N-hydroxyurea compounds
  申请人：Abbott Laboratories

  公开号：US05169854A1

  公开（公告）日：1992-12-08

  Compounds useful in inhibiting the biosynthesis of leukotrienes have the structure ##STR1## where M is hydrogen, a pharmaceutically acceptable cation, or a metabolically cleavable group, R.sup.4 is alkyl, cycloalkyl or --NR.sup.5 R.sup.6, where R.sup.5 and R.sup.6 are hydrogen, alkyl, cycloalkyl or alkanoyl, where A is a valence bond or is a straight or branched divalent alkylene group of from one to twelve carbon atoms, R.sup.2 and R.sup.3 are independently selected from hydrogen, straight or branched alkyl of from one to twelve carbon atoms, halogen, or trifluoroalkyl, and R.sup.1 is selected from phenoxy, phenylthio, 2-, 3-, or 4-pyridyloxy, 1 or 2-naphthyloxy, or 2,4,5, or 8-quinolyloxy, all optionally substituted with alkyl, haloalkyl, alkoxy, hydroxy or halogen.

  有用于抑制白三烯生物合成的化合物具有以下结构式##STR1##其中，M为氢、药学上可接受的阳离子或代谢可裂解基团，R.sup.4为烷基、环烷基或--NR.sup.5 R.sup.6，其中R.sup.5和R.sup.6为氢、烷基、环烷基或烷酰基，A为一个价键或直链或支链的二价烷基链，其碳原子数为1至12个，R.sup.2和R.sup.3独立地选择自氢、碳原子数为1至12的直链或支链烷基、卤素或三氟烷基，R.sup.1选择自苯氧基、苯硫醚基、2-、3-或4-吡啶氧基、1或2-萘氧基或2,4,5或8-喹啉氧基，所有这些基团都可以用烷基、卤代烷基、烷氧基、羟基或卤素进行取代。
• Heteroaryl cycloalkenyl hydroxyureas
  申请人：Pfizer Inc.

  公开号：US05665768A1

  公开（公告）日：1997-09-09

  Certain novel heteroaryl cycloalkenyl hydroxyurea compounds having the ability to inhibit the 5-lipoxygenase enzyme and having formula (I) and the pharmaceutically acceptable salts thereof, wherein each R.sup.1, independently, is hydrogen, hydroxy, chloro, fluoro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 haloalkoxy; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.3 is hydrogen, chloro, fluoro or C.sub.1 -C.sub.4 alkyl; X is O, S, SO or SO.sub.2 ; Z is methylene or ethylene; A is divalent radical derived from furan, thiophene, pyridine, benzofuran, benzothiophene or quinoline, or one of these groups having one substituent selected from chloro, fluoro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl and C.sub.1 -C.sub.4 haloalkoxy; n is 1, 2 or 3; and M is hydrogen or a pharmaceutically acceptable cation. These compounds are useful in the treatment or alleviation of inflammatory diseases, allergy and cardiovascular diseases in mammals and as the active ingredient in pharmaceutical compositions for treating such conditions.

  具有抑制5-脂氧合酶酶活性的某些新型杂环烷基羟基脲化合物及其药学上可接受的盐，其化学式为（I），其中每个独立的R1是氢、羟基、氯、氟、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基；R2是氢或C1-C4烷基；R3是氢、氯、氟或C1-C4烷基；X是O、S、SO或SO2；Z是亚甲基或乙烯基；A是由呋喃、噻吩、吡啶、苯并呋喃、苯并噻吩或喹啉导出的二价基团或这些基团中的一个，其中一个取代基被选择为氯、氟、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基之一；n为1、2或3；M是氢或药学上可接受的阳离子。这些化合物在哺乳动物中用于治疗或缓解炎症性疾病、过敏和心血管疾病，并作为制药组合物的活性成分用于治疗这些疾病。