2,3-dimethylfuro<3,2-b>pyrrole-5-carboxylic acid | 145161-93-9

• 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: 2,3-dimethylfuro<3,2-b>pyrrole-5-carboxylic acid
• 英文别名: 2,3-dimethyl-4H-furo[3,2-b]pyrrole-5-carboxylic acid
• CAS: 145161-93-9
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: GLXWNFBYRBJQAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 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：
  66.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dimethylfuro<3,2-b>pyrrole-5-carboxylic acid 在 三氯氧磷 作用下， 反应 6.0h， 生成 2-methyl-3-formylmethyl-4-acetylfuro<3,2-b>pyrrole
  参考文献：
  名称：

  Condensed O-, N-heterocycles by the transformation of azidoacrylates

  摘要：

  A number of furo[3,2-c]pyridines (4 a-4 d) and benzo[b]derivative (4e), as well as pyrrolo[2',3'-4,5]furo[3,2-c]pyridine (8) were prepared by reaction of the corresponding iminophosphoranes, available from ethyl azidoheteroacrylates and triphenylphosphine, with phenyl isocyanate. The appropriate azidoheteroacrylates were used for the preparation of some substituted furo[3,2-b:4,5-b]dipyrroles (6). The reactions of the prepared compounds are described.

  DOI：

  10.1007/bf00812330
• 作为产物：
  描述：

  4,5-二甲基-2-糠醛 在 sodium hydroxide 、 乙醇 、 sodium 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 5.0h， 生成 2,3-dimethylfuro<3,2-b>pyrrole-5-carboxylic acid
  参考文献：
  名称：

  Condensed O-, N-heterocycles by the transformation of azidoacrylates

  摘要：

  A number of furo[3,2-c]pyridines (4 a-4 d) and benzo[b]derivative (4e), as well as pyrrolo[2',3'-4,5]furo[3,2-c]pyridine (8) were prepared by reaction of the corresponding iminophosphoranes, available from ethyl azidoheteroacrylates and triphenylphosphine, with phenyl isocyanate. The appropriate azidoheteroacrylates were used for the preparation of some substituted furo[3,2-b:4,5-b]dipyrroles (6). The reactions of the prepared compounds are described.

  DOI：

  10.1007/bf00812330

文献信息

• Synthesis and antibacterial activity of furo[3,2-b]pyrrole derivatives
  作者：Ivana Zemanová、Renata Gašparová、Andrej Boháč、Tibor Maliar、Filip Kraic、Gabriela Addová

  DOI：10.24820/ark.5550190.p010.240

  日期：——

  synthesized by reaction of appropriate triazinone with POCl3 and subsequent treating of 8-chloro derivative with sodium ethoxide in ethanol. Furo[3,2-b]pyrrole-5carboxylates were hydrolysed to form acids, which underwent one-pot decarboxylation with TFA and formylation of the in situ formed furo[3,2-b]pyrrole with triethyl orthoformate to give 5-carbaldehydes. Hydrazinolysis of bis-esters led to bis-carbohydrazides

  8-乙氧基呋喃[2',3':4,5]吡咯并[1,2-d][1,2,4]三嗪通过适当的三嗪酮与POCl3反应，然后用乙醇钠处理8-氯衍生物合成在乙醇中。Furo[3,2-b]pyrrole-5carboxylates 水解形成酸，用 TFA 进行一锅脱羧，原位形成的 furo[3,2-b]pyrrole 与原甲酸三乙酯甲酰化得到 5-甲醛。双酯的肼解导致双碳酰肼，其随后在微波辐射下在乙酸中环化以形成具有不寻常手性的吡嗪或乙酰胺衍生物。评价制备的化合物对大肠杆菌和藤黄微球菌的抗菌活性。
• 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。
• The discovery of fused pyrrole carboxylic acids as novel, potent d-amino acid oxidase (DAO) inhibitors
  作者：Tim Sparey、Pravien Abeywickrema、Sarah Almond、Nick Brandon、Noel Byrne、Alister Campbell、Pete H. Hutson、Marlene Jacobson、Brian Jones、Sanjeev Munshi、Danette Pascarella、Andrew Pike、G. Sridhar Prasad、Nancy Sachs、Melanie Sakatis、Vinod Sardana、Shankar Venkatraman、Mary Beth Young

  DOI：10.1016/j.bmcl.2008.04.020

  日期：2008.6

  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.
• Condensed O-, N-heterocycles by the transformation of azidoacrylates
  作者：Alzbeta Krutosikova、Miloslava Dandarova、Jana Chylova、Daniel Vegh

  DOI：10.1007/bf00812330

  日期：——

  A number of furo[3,2-c]pyridines (4 a-4 d) and benzo[b]derivative (4e), as well as pyrrolo[2',3'-4,5]furo[3,2-c]pyridine (8) were prepared by reaction of the corresponding iminophosphoranes, available from ethyl azidoheteroacrylates and triphenylphosphine, with phenyl isocyanate. The appropriate azidoheteroacrylates were used for the preparation of some substituted furo[3,2-b:4,5-b]dipyrroles (6). The reactions of the prepared compounds are described.