(4-chlorophenyl)(4',5'-dihydrospiro[piperidine-4,7'-thieno[2,3-c]pyran]-1-yl)methanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (4-chlorophenyl)(4',5'-dihydrospiro[piperidine-4,7'-thieno[2,3-c]pyran]-1-yl)methanone
• 英文别名: (4-Chlorophenyl)-spiro[4,5-dihydrothieno[2,3-c]pyran-7,4'-piperidine]-1'-yl-methanone；(4-chlorophenyl)-spiro[4,5-dihydrothieno[2,3-c]pyran-7,4'-piperidine]-1'-ylmethanone
• 化学式: C₁₈H₁₈ClNO₂S
• 分子量: 347.865
• InChiKey: ZAGVXUWJEGFQCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4',5'-dihydrospiro[piperidine-4,7'-thieno[2,3-c]pyran]-1-ium trifluoroacetate 、 4-氯苯甲酰氯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以81%的产率得到(4-chlorophenyl)(4',5'-dihydrospiro[piperidine-4,7'-thieno[2,3-c]pyran]-1-yl)methanone
  参考文献：
  名称：

  Synthesis and evaluation of 4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran] analogues against both active and dormant Mycobacterium tuberculosis

  摘要：

  Need for new drugs to fight against tuberculosis (TB) is increasing day by day. In the present work we have taken a spiro compound (GSK 2200150A) reported by GSK as a lead and we modified the structure of the lead to study the antitubercular activity. For structure activity profiling twenty-one molecules have been synthesized, characterized and evaluated for their antimycobacterial potency against both active and dormant TB. Compound 06, 1-((4-methoxyphenyl) sulfonyl)-4',5'-dihydrospiro[piperidine-4,7'-thieno[2,3-c]pyran] was found to be the most potent compound (MIC: 8.23 mu M) in active TB and was less effective than the lead but more potent than standard first line drug ethambutol. It was also found to be more efficacious than Isoniazid and Rifampicin and equipotent as Moxifloxacin against dormant Mycobacterium tuberculosis (MTB). Compound 06 also showed good inhibitory potential against over expressed latent MTB enzyme lysine epsilon-amino transferase with an IC50 of 1.04 +/- 0.32 mu M. This compound is a good candidate for drug development owing to potential against both active and dormant stages of MTB. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.12.044

文献信息

• Synthesis and evaluation of 4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran] analogues against both active and dormant Mycobacterium tuberculosis
  作者：Kiran Kumar Alluri、Rudraraju Srilakshmi Reshma、Raghuram Suraparaju、Suryanarayana Gottapu、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2017.12.044

  日期：2018.5

  Need for new drugs to fight against tuberculosis (TB) is increasing day by day. In the present work we have taken a spiro compound (GSK 2200150A) reported by GSK as a lead and we modified the structure of the lead to study the antitubercular activity. For structure activity profiling twenty-one molecules have been synthesized, characterized and evaluated for their antimycobacterial potency against both active and dormant TB. Compound 06, 1-((4-methoxyphenyl) sulfonyl)-4',5'-dihydrospiro[piperidine-4,7'-thieno[2,3-c]pyran] was found to be the most potent compound (MIC: 8.23 mu M) in active TB and was less effective than the lead but more potent than standard first line drug ethambutol. It was also found to be more efficacious than Isoniazid and Rifampicin and equipotent as Moxifloxacin against dormant Mycobacterium tuberculosis (MTB). Compound 06 also showed good inhibitory potential against over expressed latent MTB enzyme lysine epsilon-amino transferase with an IC50 of 1.04 +/- 0.32 mu M. This compound is a good candidate for drug development owing to potential against both active and dormant stages of MTB. (C) 2017 Elsevier Ltd. All rights reserved.