2. Academic Validation
  3. One-pot microwave assisted stereoselective synthesis of novel dihydro-2'H-spiro[indene-2,1'-pyrrolo-[3,4-c]pyrrole]-tetraones and evaluation of their antimycobacterial activity and inhibition of AChE

One-pot microwave assisted stereoselective synthesis of novel dihydro-2'H-spiro[indene-2,1'-pyrrolo-[3,4-c]pyrrole]-tetraones and evaluation of their antimycobacterial activity and inhibition of AChE

  • Bioorg Med Chem Lett. 2017 Jul 15;27(14):3071-3075. doi: 10.1016/j.bmcl.2017.05.050.
Chelliah Bharkavi 1,  Sundaravel Vivek Kumar 1,  Mohamed Ashraf Ali 2,  Hasnah Osman 3,  Shanmugam Muthusubramanian 4,  Subbu Perumal 5
Affiliations

Affiliations

  • 1 Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, Tamil Nadu, India.
  • 2 School of Chemical Sciences, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia; New Drug Discovery Research, Department of Medicinal Chemistry, Sunrise University, Alwar, Rajasthan 301030, India.
  • 3 School of Chemical Sciences, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia.
  • 4 Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, Tamil Nadu, India. Electronic address: muthumanian2001@yahoo.com.
  • 5 Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, Tamil Nadu, India. Electronic address: subbu.perum@gmail.com.
PMID: 28552337 DOI: 10.1016/j.bmcl.2017.05.050
Abstract

An efficient one-pot microwave assisted stereoselective synthesis of novel dihydro-2'H-spiro[indene-2,1'-pyrrolo[3,4-c]pyrrole]-tetraone derivatives through three-component 1,3-dipolar cycloaddition of azomethine ylides generated in situ from ninhydrin and sarcosine with a series of 1-aryl-1H-pyrrole-2,5-diones is described. The synthesised compounds were screened for their antimycobacterial and AChE inhibition activities. Compound 4b (IC50 1.30µM) has been found to display twelve fold antimycobacterial activity compared to cycloserine and it is thirty seven times more active than pyrimethamine. Compound 4h displays maximum AChE inhibitory activity with IC50 value of 0.78±0.01µmol/L.

Keywords

1,3-Dipolar cycloaddition; AChE inhibition; Azomethine ylides; Diazabicyclic compounds; M. tuberculosis H(37)Rv.

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