5-nitro-2,3-dihydrobenzo[b]furan-7-carboxylic acid | 99517-31-4

• 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: 5-nitro-2,3-dihydrobenzo[b]furan-7-carboxylic acid
• 英文别名: 5-nitro-2,3-dihydrobenzofuran-7-carboxylic acid；5-nitro-2,3-dihydro-1-benzofuran-7-carboxylic acid
• CAS: 99517-31-4
• 化学式: C₉H₇NO₅
• 分子量: 209.158
• InChiKey: HGZXANUIYKGGSW-UHFFFAOYSA-N

物化性质

• 熔点：
  249-251.5 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  411.3±45.0 °C(Predicted)
• 密度：
  1.561±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-nitro-2,3-dihydrobenzo[b]furan-7-carboxylic acid 在 氮气 、 钯 、 水 、 氢气 作用下， 以 甲醇 为溶剂， 反应 96.33h， 以to give 5-amino-2,3-dihydrobenzo[b]furan-7-carboxylic acid (3.5 g, 19.5 mmol, 63% over 2 steps)的产率得到5-氨基-2,3-二氢-1-苯并呋喃-7-羧酸
  参考文献：
  名称：

  Compounds and their salts specific to the PPAR receptors and the EGF receptors and their use in the medical field

  摘要：

  因此，本发明特别涉及通式（I）的化合物，其中R1和R2可以相同也可以不同，选自包括H、—CnH2n-1、具有1至6个碳原子的线性或支链烷基或共同形成具有5或6个原子的芳香或脂肪环；R3选自—CO—CH3、—NHOH、—OH、—OR6，其中R6是具有1至6个碳原子的线性或支链烷基；R4选自H、具有1至6个碳原子的线性或支链烷基、苯基、苄基、—CF3或—CF2CF3、乙烯基或丙烯基；R5、R7、R8为氢原子；或R3和R4、R4和R5、或R7和R8共同形成一个环，融合到苯、芳香或脂肪环上，包括1至2个独立选择自N、O的杂原子；以及在医药领域中的使用。

  公开号：

  US20090118357A1
• 作为产物：
  描述：

  2,3-二氢苯并呋喃 在 正丁基锂 、 四甲基乙二胺 、 硝酸 、 三氟乙酸 作用下， 以 正己烷 为溶剂， 反应 7.5h， 生成 5-nitro-2,3-dihydrobenzo[b]furan-7-carboxylic acid
  参考文献：
  名称：

  Discovery and Structure–Activity Relationship of Novel 2,3-Dihydrobenzofuran-7-carboxamide and 2,3-Dihydrobenzofuran-3(2H)-one-7-carboxamide Derivatives as Poly(ADP-ribose)polymerase-1 Inhibitors

  摘要：

  Novel substituted 2,3-dihydrobenzofuran-7-carboxamide (DHBF-7-carboxamide) and 2,3-dihydrobenzofuran-3(2H)-one-7-carboxamide (DHBF-3-one-7-carboxamide) derivatives were synthesized and evaluated as inhibitors of poly(ADP-ribose)polymerase-1 (PARP-1). A structure-based design strategy resulted in lead compound 3 (DHBF-7-carboxamide; IC50 = 9.45 mu M). To facilitate synthetically feasible derivatives, an alternative core was designed, DHBF-3-one-7-carboxamide (36, IC50 = 16.2 mu M). The electrophilic 2-position of this scaffold was accessible for extended modifications. Substituted benzylidene derivatives at the 2-position were found to be the most potent, with 3',4'-dihydroxybenzylidene 58 (IC50 = 0.531 mu M) showing a 30-fold improvement in potency. Various heterocycles attached at the 4'-hydroxyl/4'-amino of the benzylidene moiety resulted in significant improvement in inhibition of PARP-1 activity (e.g., compounds 66-68, 70, 72, and 73; IC50 values from 0.718 to 0.079 mu M). Compound 66 showed selective cytotoxicity in BRCA2-deficient DT40 cells. Crystal structures of three inhibitors (compounds (-)-13c, 59, and 65) bound to a multidomain PARP-1 structure were obtained, providing insights into further development of these inhibitors.

  DOI：

  10.1021/jm5002502

文献信息

• Compounds and their salts specific to the PPAR receptors and the EGF receptors and their use in the medical field
  申请人：Naccari Giancarlo

  公开号：US20090118357A1

  公开（公告）日：2009-05-07

  Therefore the present invention relates specifically to the compounds of general formula (I), in which R 1 and R 2 , which may be identical or different, are selected from the group comprising H, —C n H 2n-1 , a linear or branched alkyl group having from 1 to 6 carbon atoms, or together form an aromatic or aliphatic ring with 5 or 6 atoms; R 3 is selected from —CO—CH 3 , —NHOH, —OH, —OR 6 in which R 6 is a linear or branched alkyl group having from 1 to 6 carbon atoms; R 4 is selected from H, a linear or branched alkyl group having from 1 to 6 carbon atoms, phenyl, benzyl, —CF 3 or —CF 2 CF 3 , vinyl or allyl; R 5 , R 7 , R 8 are hydrogen atoms; or R 3 and R 4 , R 4 and R 5 , or R 7 and R 8 together form a ring, fused to the benzene, aromatic or aliphatic ring with 5 or 6 atoms comprising from 1 to 2 heteroatoms selected independently from the group comprising N, O, and use thereof in the medical field.

  因此，本发明特别涉及具有通用公式（I）的化合物，其中R1和R2，可以相同或不同，选自包括H，—CnH2n-1，具有1到6个碳原子的直链或支链烷基，或者共同形成一个含有5或6个原子的芳香族或脂肪族环；R3选自—CO—CH3，—NHOH，—OH，—OR6，其中R6是一个具有1到6个碳原子的直链或支链烷基；R4选自H，具有1到6个碳原子的直链或支链烷基，苯基，苄基，—CF3或—CF2CF3，乙烯基或烯丙基；R5，R7，R8是氢原子；或者R3和R4，R4和R5，或R7和R8共同形成一个环，与苯环，芳香族或脂肪族环融合，含有5或6个原子，并包括1到2个独立选自N，O的杂原子，及其在医疗领域的应用。
• Development of Potent Serotonin-3 (5-HT3) Receptor Antagonists. I. Structure-Activity Relationships of 2-Alkoxy-4-amino-5-chlorobenzamide Derivatives.
  作者：Hiroshi HARADA、Toshiya MORIE、Yoshimi HIROKAWA、Naoyuki YOSHIDA、Shiro KATO

  DOI：10.1248/cpb.43.1364

  日期：——

  A new series of 2-alkoxy-4-amino-5-chlorobenzamide derivatives bearing five- to seven-membered heteroalicyclic rings in the amine moiety was synthesized and evaluated for serotonin-3 (5-HT3) receptor antagonistic activity by assaying the ability to antagonize the von Bezold-Jarisch reflex in rats. The five- to seven-membered heteroalicycles comprise pyrrolidine, morpholine, 1, 4-thiazine, piperidine, piperazine, 1, 4-oxazepine, 1, 4-thiazepine, azepine, and 1, 4-diazepine rings. Among them, some benzamide derivatives having a 1, 4-diazepine ring showed a potent 5-HT3 receptor antagonistic activity. In particular, 4-amino-5-chloro-N-(1, 4-dimethylhexahydro-1H-1, 4-diazepin-6-yl)-2-ethoxybenzamide (96) and the 1-benzyl-4-methylhexahydro-1H-1, 4-diazepine analogue 103 showed potent 5-HT3 receptor antagonistic activity without 5-HT4 receptor binding affinity.

  合成了一系列新的2-烷氧基-4-氨基-5-氯苯甲酰胺衍生物，这些衍生物在氨基部分包含五到七元的杂环非芳香环，并通过测试其对大鼠冯·贝佐尔德-雅里希反射的拮抗能力来评估其对血清素-3（5-HT3）受体的拮抗活性。五到七元的杂环包括吡咯烷、吗啉、1,4-噻嗪、哌啶、哌嗪、1,4-噁唑烯、1,4-噻唑烯、七元环及1,4-二唑烯环。其中，某些具有1,4-二唑烯环的苯甲酰胺衍生物表现出了强效的5-HT3受体拮抗活性。特别是4-氨基-5-氯-N-(1,4-二甲基六氢-1H-1,4-二唑啉-6-基)-2-乙氧基苯甲酰胺（96）和1-苄基-4-甲基六氢-1H-1,4-二唑啉类似物103展现了强效的5-HT3受体拮抗活性，而未表现出对5-HT4受体的结合亲和力。
• Carboxamides useful as antiemetic or antipsychotic agents
  申请人：Erbamont, Inc.

  公开号：US04888353A1

  公开（公告）日：1989-12-19

  Carboxamides represented by the formula (I): ##STR1## wherein Z represents the carbon atoms necessary to complete a 5- to 7-membered ring, R.sup.1, R.sup.2, and R.sup.3 may be the same or different and are selected from the group consisting of a hydrogen atom, a lower alkyl group, a cycloalkyl group, a halogen atom, an amino group, a lower alkylamino group, an alkoxy group, an acylamido group, a sulfonamido group, and a nitro group; and A represents an aminoalkyl moiety and acid addition salts thereof.

  由公式(I)表示的羧酰胺：##STR1##其中Z代表完成5-到7-成员环所需的碳原子，R.sup.1、R.sup.2和R.sup.3可能相同也可能不同，选自氢原子、较低的烷基、环烷基、卤原子、氨基、较低的烷基氨基、烷氧基、酰胺基、磺胺基和硝基的群；A代表氨基烷基基团及其酸盐。
• Compounds and their Salts Specific to the PPAR Receptors and the EGF Receptors and their Use in the Medical Field
  申请人：Naccari Giancarlo

  公开号：US20120316230A1

  公开（公告）日：2012-12-13

  The present invention relates to compounds of formula (I), where R 1 and R 2 , which may be identical or different, are selected from the group comprising H, C n H 2n-1 , a linear or branched alkyl group having 1 to 6 carbons, or together form an aromatic or aliphatic ring with 5 or 6 atoms; R 3 is —CO—CH 3 , —NHOH, —OH, or —OR 6 where R 6 is a linear or branched alkyl group having 1 to 6 carbon atoms; R4 is H, linear or branched alkyl group having from 1 to 6 atoms, phenyl, benzyl, —CF 3 or CF 2 CF 3 , vinyl or allyl; R 5 , R 7 , R 8 are hydrogen atoms; or R 3 and R 4 , R 4 and R 5 , or R 7 and R 8 together form a ring, fused to the benzene, aromatic or aliphatic ring with 5 or 6 atoms comprising from 1 to 2 heteroatoms selected independently from the group comprising N, O, and use thereof in the medical field.

  本发明涉及式（I）的化合物，其中R1和R2，可以相同也可以不同，选择自H，CnH2n-1，具有1至6个碳的线性或支链烷基团，或者共同形成一个具有5或6个原子的芳香或脂肪环；R3为—CO—CH3，—NHOH，—OH或—OR6，其中R6为具有1至6个碳的线性或支链烷基团；R4为H，具有1至6个原子的线性或支链烷基团，苯基，苄基，—CF3或CF2CF3，乙烯基或丙烯基；R5，R7，R8为氢原子；或者R3和R4，R4和R5，或R7和R8共同形成一个环，与苯环，芳香或脂肪环共同构成一个具有1至2个杂原子的环，独立选择自N，O的群组；以及在医药领域中的应用。
• Compounds and their salts specific to the PPAR receptors and the EGF Receptors and their use in the medical field
  申请人：Naccari Giancarlo

  公开号：US08450506B2

  公开（公告）日：2013-05-28

  The present invention relates to compounds of formula (I), where R1 and R2, which may be identical or different, are selected from the group comprising H, CnH2n-1, a linear or branched alkyl group having 1 to 6 carbons, or together form an aromatic or aliphatic ring with 5 or 6 atoms; R3 is —CO—CH3, —NHOH, —OH, or —OR6 where R6 is a linear or branched alkyl group having 1 to 6 carbon atoms; R4 is H, linear or branched alkyl group having from 1 to 6 atoms, phenyl, benzyl, —CF3 or CF2CF3, vinyl or allyl; R5, R7, R8 are hydrogen atoms; or R3 and R4, R4 and R5, or R7 and R8 together form a ring, fused to the benzene, aromatic or aliphatic ring with 5 or 6 atoms comprising from 1 to 2 heteroatoms selected independently from the group comprising N, O, and use thereof in the medical field.

  本发明涉及化合物的公式（I），其中R1和R2可以相同也可以不同，选自包括H、CnH2n-1、具有1到6个碳原子的线性或支链烷基或共同形成具有5或6个原子的芳香或脂肪环；R3是-CO-CH3、-NHOH、-OH或-OR6，其中R6是具有1到6个碳原子的线性或支链烷基；R4是H、具有1到6个原子的线性或支链烷基、苯基、苄基、-CF3或CF2CF3、乙烯基或丙烯基；R5、R7、R8是氢原子；或R3和R4、R4和R5或R7和R8共同形成一个环，与苯、芳香或脂肪环共同构成具有1到2个杂原子（独立选自包括N、O的群）的环，并在医学领域中使用。