ethyl 3-chloro-4H-furo[3,2-b]pyrrole-5-carboxylate | 1007388-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡咯
• 英文名称: ethyl 3-chloro-4H-furo[3,2-b]pyrrole-5-carboxylate
• CAS: 1007388-13-7
• 化学式: C₉H₈ClNO₃
• 分子量: 213.62
• InChiKey: GMQBSQREBGIUFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-chloro-4H-furo[3,2-b]pyrrole-5-carboxylate 在 sodium hydroxide 作用下， 生成 3-chloro-4H-furo[3,2-b]pyrrole-5-carboxylic acid
  参考文献：
  名称：

  The discovery of fused pyrrole carboxylic acids as novel, potent d-amino acid oxidase (DAO) inhibitors

  摘要：

  The 'NMDA hypofunction hypothesis of schizophrenia' can be tested in a number of ways. DAO is the enzyme primarily responsible for the metabolism of d-serine, a co-agonist for the NMDA receptor. We identified novel DAO inhibitors, in particular, acid 1, which demonstrated moderate potency for DAO in vitro and ex vivo, and raised plasma d-serine levels after dosing ip to rats. In parallel, analogues were prepared to survey the SARs of 1.

  DOI：

  10.1016/j.bmcl.2008.04.020
• 作为产物：
  描述：

  C₉H₈ClN₃O₃ 以 甲苯 为溶剂， 生成 ethyl 3-chloro-4H-furo[3,2-b]pyrrole-5-carboxylate
  参考文献：
  名称：

  The discovery of fused pyrrole carboxylic acids as novel, potent d-amino acid oxidase (DAO) inhibitors

  摘要：

  The 'NMDA hypofunction hypothesis of schizophrenia' can be tested in a number of ways. DAO is the enzyme primarily responsible for the metabolism of d-serine, a co-agonist for the NMDA receptor. We identified novel DAO inhibitors, in particular, acid 1, which demonstrated moderate potency for DAO in vitro and ex vivo, and raised plasma d-serine levels after dosing ip to rats. In parallel, analogues were prepared to survey the SARs of 1.

  DOI：

  10.1016/j.bmcl.2008.04.020
• 作为试剂：
  描述：

  3-溴-4H-呋喃并[3,2-b]吡咯-5-甲酸乙酯 、 ethyl 3-chloro-4H-thieno[3,2-b]pyrrole-5-carboxylate 在 ethyl 3-chloro-4H-furo[3,2-b]pyrrole-5-carboxylate 、 silica gel 作用下， 以 ethyl acetate heptane 为溶剂， 生成 ethyl 3-chloro-4H-furo[3,2-b]pyrrole-5-carboxylate
  参考文献：
  名称：

  FLUORO-SUBSTITUTED INHIBITORS OF D-AMINO ACID OXIDASE

  摘要：

  本发明提供了新型D-氨基酸氧化酶抑制剂，以及包括该发明化合物的制药组合物。本发明还提供了治疗和预防神经系统疾病，如神经精神疾病和神经退行性疾病，以及疼痛、共济失调和惊厥的方法。该发明化合物具有以下一般结构：其中A为NH或S，Q为从CR1和N中选择的成员，X和Y是独立选择的成员，选择自O、S、CR2、N和NH。R1、R2和R4是独立选择的成员，选择自H和F，但至少选择R1、R2和R4中的一个成员为F。R6为从O-X+和OH中选择的成员，其中X+为正离子，选择自无机正离子和有机正离子。

  公开号：

  US20080004327A1

文献信息

• Fused heterocyclic inhibitors of D-amino acid oxidase
  申请人：Heffernan L. R. Michele

  公开号：US20080058395A1

  公开（公告）日：2008-03-06

  This invention provides novel inhibitors of the enzyme D-amino acid oxidase as well as pharmaceutical compositions including the compounds of the invention. Also provided are methods for the treatment and prevention of neurological disorders, such as neuropsychiatric and neurodegenerative diseases, as well as pain, ataxia and convulsion. The compounds of the invention have the general structure: wherein Q is a member selected from O, S, CR 1 and N, X and Y are members independently selected from CR 2 , O, S, N and NR 3 .

  本发明提供了D-氨基酸氧化酶的新型抑制剂，以及包括该发明化合物的制药组合物。同时，还提供了治疗和预防神经系统疾病，如神经精神疾病和神经退行性疾病，以及疼痛、共济失调和惊厥的方法。该发明化合物具有以下一般结构：其中Q是从O、S、CR1和N中选择的成员，X和Y是独立选择自CR2、O、S、N和NR3的成员。
• Fluoro-substituted inhibitors of D-amino acid oxidase
  申请人：Sepracor Inc.

  公开号：US07884124B2

  公开（公告）日：2011-02-08

  This invention provides novel inhibitors of the enzyme D-amino acid oxidase as well as pharmaceutical compositions including the compounds of the invention. The invention also provides methods for the treatment and prevention of neurological disorders, such as neuropsychiatric and neurodegenerative diseases, as well as pain, ataxia and convulsion. The compounds of the invention have the general structure: wherein A is NH or S. Q is a member selected from CR1 and N. X and Y are members independently selected from O, S, CR2, N and NH. R1, R2 and R4 are members independently selected from H and F, provided that at least one member selected from R1, R2 and R4 is F. R6 is a member selected from O−X+ and OH, wherein X+ is a positive ion, which is a member selected from inorganic positive ions and organic positive ions.

  本发明提供了D-氨基酸氧化酶的新型抑制剂，以及包括本发明化合物的制药组合物。本发明还提供了用于治疗和预防神经系统疾病，如神经精神疾病和神经退行性疾病，以及疼痛、共济失调和抽搐的方法。本发明化合物具有以下一般结构： 其中A为NH或S。Q为选择自CR1和N的成员。X和Y是独立选择自O、S、CR2、N和NH的成员。R1、R2和R4是独立选择自H和F的成员，但至少选择自R1、R2和R4中的一个成员为F。R6为选择自O−X+和OH的成员，其中X+为正离子，其为选择自无机正离子和有机正离子的成员。
• US7884124B2
  申请人：——

  公开号：US7884124B2

  公开（公告）日：2011-02-08
• [EN] FUSED HETEROCYCLIC INHIBITORS OF D-AMINO ACID OXIDASE<br/>[FR] INHIBITEURS HÉTÉROCYCLIQUES FUSIONNÉS DE LA D-AMINOACIDE-OXYDASE
  申请人：SEPRACOR INC

  公开号：WO2008005456A2

  公开（公告）日：2008-01-10

  [EN] This invention provides novel inhibitors of the enzyme D-amino acid oxidase as well as pharmaceutical compositions including the compounds of the invention. Also provided are methods for the treatment and prevention of neurological disorders, such as neuropsychiatric and neurodegenerative diseases, as well as pain, ataxia and convulsion. The compounds of the invention have the general structure wherein Q is a member selected from O, S, CR¹ and N, X and Y are members independently selected from CR², O, S, N and NR³.
  [FR] La présente invention concerne des inhibiteurs innovants de l'enzyme D-aminoacide-oxydase ainsi que des compositions pharmaceutiques qui comprennent les composés de l'invention. L'invention concerne également des procédés de traitement et de prévention de troubles neurologiques, tels que des maladies neuropsychiatriques et neurodégénératives, de même que de la douleur, de l'ataxie et des convulsions. Les composés selon l'invention présentent la structure générale dans laquelle Q est choisi parmi O, S, CR¹ et N, X et Y sont choisis indépendamment parmi CR², O, S, N et NR³.