6,7-dihydro-4H-thieno[3,2-c]pyran-2-carbaldehyde | 623564-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡喃类
• 英文名称: 6,7-dihydro-4H-thieno[3,2-c]pyran-2-carbaldehyde
• CAS: 623564-80-7
• 化学式: C₈H₈O₂S
• 分子量: 168.216
• InChiKey: DONVCZPIYCTGFE-UHFFFAOYSA-N

物化性质

• 沸点：
  339.9±42.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7-dihydro-4H-thieno[3,2-c]pyran-2-carbaldehyde 在 palladium on activated charcoal phosphate buffer 、 氢气 、 三乙胺 、 magnesium bromide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， -20.0 ℃ 、310.26 kPa 条件下， 反应 27.0h， 生成 6-(6,7-dihydro-4H-thieno[3,2-c]pyran-2-ylmethylene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt
  参考文献：
  名称：

  Structure-Activity Relationship of 6-Methylidene Penems Bearing 6,5 Bicyclic Heterocycles as Broad-Spectrum β-Lactamase Inhibitors:  Evidence for 1,4-Thiazepine Intermediates with C7 R Stereochemistry by Computational Methods

  摘要：

  The design and synthesis of a series of 6-methylidene penems containing [6,5]-fused bicycles (thiophene, imidazole, or pyrazle-fused system) as novel class A, B, and C beta-lactamase inhibitors is described. These penems proved to be potent inhibitors of the TEM-1 (class A) and AmpC (class C) beta-lactamases and less so against the class B metallo-beta-lactamase CcrA. Their in vitro and in vivo activities in combination with piperacillin are discussed. On the basis of the crystallographic structures of a serine-bound reaction intermediate of 2 with SHV-1 (class A) and GC1 (class C) enzymes, compounds 14a-1 were designed and synthesized. Penems are proposed to form a seven-membered 1,4 thiazepine ring in both class A and C beta-lactamases. The interaction energy calculation for the enzyme-bound intermediates favor the formation of the C7 R enantiomer over the S enantiomer of the 1,4-thiazepine in both beta-lactamases, which is consistent with those obtained from the crystal structure of 2 with SHV-1 and GC1.

  DOI：

  10.1021/jm060021p
• 作为产物：
  描述：

  吡喃-4-酮 在 N,N-二甲基甲酰胺 三氯氧磷 、 三乙胺 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 二氯甲烷 为溶剂， 反应 22.1h， 以14%的产率得到6,7-dihydro-4H-thieno[3,2-c]pyran-2-carbaldehyde
  参考文献：
  名称：

  [EN] PROCESS FOR PREPARING 6-ALKYLIDENE PENEM DERIVATIVES
  [FR] PROCEDE DE PREPARATION DE DERIVES DE 6-ALKYLIDENE PENEM

  摘要：

  本发明提供了一种制备化合物的方法，该化合物符合式（I），对于治疗细菌感染或疾病非常有用。

  公开号：

  WO2003093277A1

文献信息

• Process for preparing 6-alkylidene penem derivatives
  申请人：Wyeth

  公开号：US20040132708A1

  公开（公告）日：2004-07-08

  The present invention provides a process of making compounds of formula I, which are useful for the treatment of bacterial infection or disease. 1

  本发明提供了一种制备式I化合物的方法，该化合物对治疗细菌感染或疾病有用。
• Bicyclic 6-alkylidene-penems as class-D beta-lactamases inhibitors
  申请人：Mansour Suhayl Tarek

  公开号：US20060276445A1

  公开（公告）日：2006-12-07

  This invention relates to certain bicyclic 6-alkylidene penems which act as a inhibitor of class-D enzymes. β-Lactamases hydrolyze β-lactam antibiotics, and as such serve as the primary cause of bacterial resistance. The compounds of the present invention when combined with β-lactam antibiotics will provide an effective treatment against life threatening bacterial infections. In accordance with the present invention there are provided compounds of general formula I or a pharmaceutically acceptable salt or in vivo hydrolyzable ester R 5 thereof: wherein: One of A and B denotes hydrogen and the other an optionally substituted fused bicyclic heteroaryl group; and X═O or S.

  这项发明涉及某些具有双环6-烷基亚烯基青霉素结构的化合物，其作为D类酶的抑制剂。β-内酰胺酶水解β-内酰胺类抗生素，因此是细菌耐药的主要原因。本发明的化合物与β-内酰胺类抗生素结合后，将提供一种有效的治疗方法，用于治疗威胁生命的细菌感染。根据本发明，提供了一般式I的化合物，或其药学上可接受的盐或体内可水解的酯R5：其中：A和B中的一个表示氢，另一个表示可选择取代的融合双环杂环芳基团；X＝O或S。
• [EN] BICYCLIC 6-ALKYLIDENE-PENEMS AS ß-LACTAMASES INHIBITORS<br/>[FR] PENEMES 6-ALKYLIDENE BICYCLIQUES UTILISES EN TANT QU'INHIBITEURS DE ss-LACTAMASES
  申请人：WYETH CORP

  公开号：WO2003093279A1

  公开（公告）日：2003-11-13

  The present invention provides a compound of Formula (I), pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.

  本发明提供了一种化合物（I）的配方、药物组合物以及其用于治疗患有细菌感染或疾病的患者的用途。
• [EN] PROCESS FOR PREPARING 6-ALKYLIDENE PENEM DERIVATIVES<br/>[FR] PROCEDE DE PREPARATION DE DERIVES DE 6-ALKYLIDENE PENEM
  申请人：WYETH CORP

  公开号：WO2003093277A1

  公开（公告）日：2003-11-13

  The present invention provides a process of making compounds of Formula (I), which are useful for the treatment of bacterial infection or disease.

  本发明提供了一种制备化合物的方法，该化合物符合式（I），对于治疗细菌感染或疾病非常有用。
• Bicyclic 5-alkylidene-penems as beta lactamases inhibitors
  申请人：Wyeth

  公开号：US20040077622A1

  公开（公告）日：2004-04-22

  The present invention provides a compound of formula 1, pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof. 1

  本发明提供了一种化合物1，其制备药物组合物并用于治疗需要治疗细菌感染或疾病的患者。