2-butyl-7-methoxy-benzofuran-4-carboxylic acid | 185407-33-4

• 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: 2-butyl-7-methoxy-benzofuran-4-carboxylic acid
• 英文别名: 2-Butyl-7-methoxy-1-benzofuran-4-carboxylic acid
• CAS: 185407-33-4
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: KJSACBIEOWLHMW-UHFFFAOYSA-N

物化性质

• 沸点：
  393.2±37.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-butyl-7-methoxy-benzofuran-4-carboxylic acid 在 草酰氯 、 sodium aluminum diethyl dihydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.75h， 生成 2-丁基-N-(3,5-二氯吡啶-4-基)-7-甲氧基-1-苯并呋喃-4-甲酰胺
  参考文献：
  名称：

  Benzofuran based PDE4 inhibitors

  摘要：

  Replacement of the 3,4-dialkoxyphenyl substructure common to a number of PDE4 inhibitors with a 2-alkyl-7-methoxybenzofuran unit is described. This substitution can result in either enhancement or substantial reductions in PDE4 inhibitory activity depending on the system to which it is applied. An in vitro SAR study of a potent series of 4-(2-heteroaryl-ethyl)-benzofurans 26 is also presented. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00038-3
• 作为产物：
  描述：

  2-溴-3-羟基-4-甲氧基苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium chlorite 、 sodium dihydrogenphosphate 、 copper(l) iodide 、 2-甲基-2-丁烯 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 5.5h， 生成 2-butyl-7-methoxy-benzofuran-4-carboxylic acid
  参考文献：
  名称：

  Benzofuran based PDE4 inhibitors

  摘要：

  Replacement of the 3,4-dialkoxyphenyl substructure common to a number of PDE4 inhibitors with a 2-alkyl-7-methoxybenzofuran unit is described. This substitution can result in either enhancement or substantial reductions in PDE4 inhibitory activity depending on the system to which it is applied. An in vitro SAR study of a potent series of 4-(2-heteroaryl-ethyl)-benzofurans 26 is also presented. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00038-3

文献信息

• DERIVATIVES OF BENZOFURAN OR BENZODIOXOLE
  申请人：——

  公开号：US20020128290A1

  公开（公告）日：2002-09-12

  An oxygen-containing heterocyclic compound represented by following Formula (I): 1 wherein R 1 and R 2 independently represent hydrogen, lower alkyl, cyano, —(CH 2 ) n —E 1 —CO—G 1 (wherein E 1 represents a bond, O, or NH; and G 1 represents hydrogen, substituted or unsubstituted lower alkyl, OR 6 , or NR 7 R 8 ; and n represents an integer of 0 to 4), or the like; R 1 and R 2 are combined to represent a saturated carbon ring together with a carbon atom adjacent thereto; or R 2 , and R 11 or R 13 described below are combined to form a single bond; R 3 represents hydrogen, phenyl, or halogen; R 4 represents hydroxy, lower alkoxy, or the like; A represents —C(R 9 )(R 10 )— or O; B represents O, NR 11 , —C(R 12 )(R 13 )—, or —C(R 14 )(R 15 )—C(R 16 )(R 17 )—; D represents (i) —C(R 18 )(R 19 )—X— (wherein X represents —C(R 21 )(R 22 )—, S, or NR 23 ), (ii) —C(R 19a )═Y— [Y represents —C(R 24 )—Z— (wherein Z represents CONH, CONHCH 2 , or a bond), or N], or (iii) a bond; and R 5 represents aryl, an aromatic heterocyclic group, cycloalkyl, pyridine-N-oxide, cyano, or lower alkoxycarbonyl; or pharmaceutically acceptable salts thereof.

  以下是由下式（I）表示的含氧杂环化合物： 其中R1和R2独立地表示氢、较低的烷基、氰基、—（CH2）n—E1—CO—G1（其中E1表示键、O或NH；G1表示氢、取代或未取代的较低烷基、OR6或NR7R8；n表示0到4的整数），或类似物；R1和R2结合表示与相邻碳原子一起形成饱和碳环；或R2，以及下文描述的R11或R13结合形成单键；R3表示氢、苯基或卤素；R4表示羟基、较低的烷氧基或类似物；A表示—C（R9）（R10）—或O；B表示O、NR11、—C（R12）（R13）—或—C（R14）（R15）—C（R16）（R17）—；D表示（i）—C（R18）（R19）—X—（其中X表示—C（R21）（R22）—、S或NR23）、（ii）—C（R19a）═Y—［Y表示—C（R24）—Z—（其中Z表示CONH、CONHCH2或键），或N］，或（iii）键；R5表示芳基、芳香杂环基、环烷基、吡啶-N-氧化物、氰基或较低烷氧羰基；或其药学上可接受的盐。
• PYRIDO(3,2-D)PYRIMIDINES AND PHARMACEUTICAL COMPOSITIONS USEFUL FOR MEDICAL TREATMENT
  申请人：De Jonghe Steven Cesar Alfons

  公开号：US20090036430A1

  公开（公告）日：2009-02-05

  This invention relates to substituted pyrido(3,2-d)pyrimidine derivatives, their pharmaceutically acceptable salts, N-oxides, solvates, pro-drugs and enantiomers, possessing unexpectedly desirable pharmaceutical properties, in particular which are highly active immunosuppressive agents, and as such are useful in the treatment in transplant rejection and/or in the treatment of certain inflammatory diseases. These derivatives are also useful in preventing or treating cardiovascular disorders, disorders of the central nervous system, TNF-α related disorders, viral diseases (including hepatitis C), erectile dysfunction and cell proliferative disorders.

  本发明涉及取代的吡啶并(3,2-d)嘧啶衍生物、它们的药学上可接受的盐、N-氧化物、溶剂化合物、前药和对映体，具有意外的理想药理特性，特别是高度活性的免疫抑制剂，因此在移植排斥和/或治疗某些炎症性疾病方面非常有用。这些衍生物还可用于预防或治疗心血管疾病、中枢神经系统疾病、TNF-α相关疾病、病毒性疾病（包括丙型肝炎）、勃起功能障碍和细胞增殖性疾病。
• OXYGEN-CONTAINING HETEROCYCLIC COMPOUNDS
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0771794A1

  公开（公告）日：1997-05-07

  An oxygen-containing heterocyclic compound represented by following Formula (I): wherein R1 and R2 independently represent hydrogen, lower alkyl, cyano, -(CH2)n-E-CO-F (wherein E represents a bond, O, or NH; F represents OR6 or NR7R8; and n represents an integer of 0 to 4), or the like; R1 and R2 are combined to represent a saturated carbon ring together with a carbon atom adjacent thereto; or R2, and R11 or R13 described below are combined to form a single bond; R3 represents hydrogen, phenyl, or halogen; R4 represents hydroxy, lower alkoxy, or the like; A represents -C(R9)(R10)- or O; B represents O, NR11, -C(R12)(R13)-, or -C(R14)(R15)-C(R16)(R17)-; D represents (i) -C(R18)(R19)-X- (wherein X represents -C(R21)(R22)-, S, or NR23), (ii) -C(R19a)=Y- [Y represents -C(R24)-Z- (wherein Z represents CONH, CONHCH2, or a bond), or N], or (iii) a bond; and R5 represents aryl, an aromatic heterocyclic group, cycloalkyl, pyridine-N-oxide, cyano, or lower alkoxycarbonyl; or a pharmaceutically acceptable salt thereof.

  由下式（I）代表的含氧杂环化合物： 其中 R1 和 R2 独立地代表氢、低级烷基、氰基、-(CH2)n-E-CO-F（其中 E 代表键、O 或 NH；F 代表 OR6 或 NR7R8；n 代表 0 至 4 的整数）或类似物；R1 和 R2 结合在一起代表一个饱和碳环及其邻近的碳原子；或 R2 和下述 R11 或 R13 结合在一起形成单键；R3 代表氢、苯基或卤素；R4 代表羟基、低级烷氧基或类似物；A 代表-C(R9)(R10)-或 O；B 代表 O、NR11、-C(R12)(R13)-或-C(R14)(R15)-C(R16)(R17)-；D 代表 (i) -C(R18)(R19)-X- （其中 X 代表 -C(R21)(R22)-、S 或 NR23），(ii) -C(R19a)=Y- [Y 代表 -C(R24)-Z- （其中 Z 代表 CONH、CONHCH2 或键）或 N]，或 (iii) 键；R5 代表芳基、芳香杂环基团、环烷基、吡啶-N-氧化物、氰基或低级烷氧羰基；或其药学上可接受的盐。
• Administration of phosphodiesterase inhibitors for the treatment of premature ejaculation
  申请人：——

  公开号：US20020037828A1

  公开（公告）日：2002-03-28

  A method is provided for treatment of premature ejaculation by administration of a phosphodiesterase inhibitor, e.g., an inhibitor of a Type III, Type IV, or Type V phosphodiesterase. In a preferred embodiment, administration is on as “as needed” basis, i.e., the drug is administered immediately or several hours prior to sexual activity. Pharmaceutical formulations and packaged kits are also provided.

  提供了一种通过施用磷酸二酯酶抑制剂（例如，III型、IV型或V型磷酸二酯酶抑制剂）治疗早泄的方法。在一个优选的实施方案中，根据 "需要 "给药，即在性活动前立即或数小时给药。此外，还提供药物制剂和包装套件。
• Transmucosal phosphodiesterase inhibitors for the treatment of erectile dysfunction
  申请人：——

  公开号：US20030134861A1

  公开（公告）日：2003-07-17

  A pharmaceutical formulation is provided for treating erectile dysfunction in a mammalian male individual. The pharmaceutical formulation includes a phosphodiesterase inhibitor or a pharmaceutically acceptable salt, ester, amide or derivative thereof, that is administered transmucosally within the context of an effective dosing regimen. Preferred modes of administration include transbuccal, sublingual and transrectal routes. A kit for the administration of the pharmaceutical formulation is also provided.

  提供了一种治疗哺乳动物男性个体勃起功能障碍的药物制剂。该药物制剂包括一种磷酸二酯酶抑制剂或其药学上可接受的盐、酯、酰胺或衍生物，在有效给药方案内经粘膜给药。优选的给药方式包括经口腔、舌下和经直肠途径。此外，还提供了一种用于施用药物制剂的试剂盒。