thieno[3,2-b]pyrrole-5-carbaldehyde | 1404187-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡咯类
• 英文名称: thieno[3,2-b]pyrrole-5-carbaldehyde
• 英文别名: 4H-thieno[3,2-b]pyrrole-5-carbaldehyde
• CAS: 1404187-18-3
• 化学式: C₇H₅NOS
• 分子量: 151.189
• InChiKey: FHSZDHJXKBJLLT-UHFFFAOYSA-N

物化性质

• 沸点：
  350.3±22.0 °C(Predicted)
• 密度：
  1.467±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  thieno[3,2-b]pyrrole-5-carbaldehyde 在 三乙胺 、 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 16.17h， 生成
  参考文献：
  名称：

  Development of non-symmetric thiophene-fused BODIPYs

  摘要：

  A series of non-symmetric BODIPYs containing thieno[3,2-b]pyrrole moiety were synthesized in 21-63% yields. The absorption and emission maxima covered from the visible green to red region (lambda(abs)=532-647 nm: lambda(em)=547-664 nm; Phi(f)=0.19-0.45). X-ray analysis indicated that the S-C bond lengths were shorter than those of thienopyrrole and thienohelicene by 0.03-0.05 angstrom. The crystal packing pattern suggested that strong pi-pi interaction, intermolecular C-H center dot center dot center dot F interaction, and weak S center dot center dot center dot pi interaction existed. The tunable emission was achieved by structure modifications. Oxidation of BODIPY (lambda(em)=547 nm) with m-CPBA generated thiophene-1,1-dioxide derived BODIPY (lambda(em)=528 nm). Knoevenagel-type condensation of BODIPY with N,N-dimethylaminobenzaldehyde led to BODIPY (lambda(em)=693 nm) with extended conjugation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.011
• 作为产物：
  描述：

  4H-噻吩[3,2-b]吡咯-5-羧酸乙酯 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 thieno[3,2-b]pyrrole-5-carbaldehyde
  参考文献：
  名称：

  Development of non-symmetric thiophene-fused BODIPYs

  摘要：

  A series of non-symmetric BODIPYs containing thieno[3,2-b]pyrrole moiety were synthesized in 21-63% yields. The absorption and emission maxima covered from the visible green to red region (lambda(abs)=532-647 nm: lambda(em)=547-664 nm; Phi(f)=0.19-0.45). X-ray analysis indicated that the S-C bond lengths were shorter than those of thienopyrrole and thienohelicene by 0.03-0.05 angstrom. The crystal packing pattern suggested that strong pi-pi interaction, intermolecular C-H center dot center dot center dot F interaction, and weak S center dot center dot center dot pi interaction existed. The tunable emission was achieved by structure modifications. Oxidation of BODIPY (lambda(em)=547 nm) with m-CPBA generated thiophene-1,1-dioxide derived BODIPY (lambda(em)=528 nm). Knoevenagel-type condensation of BODIPY with N,N-dimethylaminobenzaldehyde led to BODIPY (lambda(em)=693 nm) with extended conjugation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.011

文献信息

• FLUORO-SUBSTITUTED INHIBITORS OF D-AMINO ACID OXIDASE
  申请人：Heffernan L. R. Michele

  公开号：US20080004327A1

  公开（公告）日：2008-01-03

  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 CR 1 and N. X and Y are members independently selected from O, S, CR 2 , N and NH. R 1 , R 2 and R 4 are members independently selected from H and F, provided that at least one member selected from R 1 , R 2 and R 4 is F. R 6 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.

  这项发明提供了D-氨基酸氧化酶的新型抑制剂，以及包括该发明中化合物的药物组合物。该发明还提供了用于治疗和预防神经系统疾病，如神经精神病和神经退行性疾病，以及疼痛、共济失调和抽搐的方法。该发明中的化合物具有一般结构：其中A为NH或S。Q是从CR1和N中选择的成员。X和Y分别是从O、S、CR2、N和NH中独立选择的成员。R1、R2和R4是从H和F中独立选择的成员，前提是至少选择R1、R2和R4中的一个成员为F。R6是从O−X+和OH中选择的成员，其中X+是正离子，从无机正离子和有机正离子中选择的成员。
• 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。
• ACTIVATORS OF HUMAN PYRUVATE KINASE
  申请人：Thomas Craig J.

  公开号：US20120245141A1

  公开（公告）日：2012-09-27

  Disclosed are pyruvate kinase M2 activators, which are, bis sulfonamide piperazinyl compounds of Formula (I) and 2,4-disubstituted 4H-thieno[3,2-b]pyrrole-2-(substituted benzyl)pyridazin-3(2H)ones of Formula (II), wherein L and R 1 to R 16 are as defined herein, that are useful in treating a number of diseases that are treatable by the activation of PKM2, for example, cancer and anemia,

  本发明涉及丙酮酸激酶M2激活剂，其为式（I）的双磺酰胺哌嗪化合物和式（II）的2,4-二取代4H-噻吩[3,2-b]吡咯-2-(取代苄基)吡啶并[3(2H)]酮，其中L和R1至R16如本文所定义，可用于治疗许多可通过激活PKM2治疗的疾病，例如癌症和贫血。
• US7884124B2
  申请人：——

  公开号：US7884124B2

  公开（公告）日：2011-02-08
• Development of non-symmetric thiophene-fused BODIPYs
  作者：Xin-Dong Jiang、Houjun Zhang、Yuanlin Zhang、Weili Zhao

  DOI：10.1016/j.tet.2012.09.011

  日期：2012.11

  A series of non-symmetric BODIPYs containing thieno[3,2-b]pyrrole moiety were synthesized in 21-63% yields. The absorption and emission maxima covered from the visible green to red region (lambda(abs)=532-647 nm: lambda(em)=547-664 nm; Phi(f)=0.19-0.45). X-ray analysis indicated that the S-C bond lengths were shorter than those of thienopyrrole and thienohelicene by 0.03-0.05 angstrom. The crystal packing pattern suggested that strong pi-pi interaction, intermolecular C-H center dot center dot center dot F interaction, and weak S center dot center dot center dot pi interaction existed. The tunable emission was achieved by structure modifications. Oxidation of BODIPY (lambda(em)=547 nm) with m-CPBA generated thiophene-1,1-dioxide derived BODIPY (lambda(em)=528 nm). Knoevenagel-type condensation of BODIPY with N,N-dimethylaminobenzaldehyde led to BODIPY (lambda(em)=693 nm) with extended conjugation. (C) 2012 Elsevier Ltd. All rights reserved.