Medicinal Chemistry Research

, Volume 26, Issue 10, pp 2592–2601 | Cite as

Synthesis, characterization, antimicrobial and anti-biofilm activity of a new class of 11-bromoundecanoic acid-based betaines

  • Sathyam Reddy Yasa
  • Y. Poornachandra
  • C. Ganesh Kumar
  • Vijayalakshmi Penumarthy
Original Research


Novel betaines were synthesized from esterquats, which in turn were obtained from the reaction of 11-bromo undecanoic acid, different alkyl amines, and methyl iodide. The synthesized betaines were characterized by fourier transform infrared, proton nuclear magnetic resonance, carbon-13 nuclear magnetic resonance, and mass spectral analysis. These betaines were synthesized in four steps; in the first step, 11-bromo undecanoic acid was converted into methyl 11-bromoundecanoate followed by the synthesis of secondary amine monoester, and tertiary amine mono and diesters by the reaction of 11-bromoundecanoate with different aliphatic amines (hexyl, dodecyl, octadecyl, dioctyl, and dicyclohexyl amine). In the third step, the prepared secondary amine monoesters, tertiary amine mono, and diesters were converted into monoesterquats and diesterquats by reacting with methyl iodide. The resultant esterquats were converted into betaines by saponification reaction using LiOH.H2O in water and tetrahydrofuran. The synthesized compounds (5ah) were studied for their antimicrobial activity. Some of the compounds showed good to moderate antibacterial activity with minimum inhibitory concentration values ranging between 3.9–31.2 µg mL−1 and antifungal activity with minimum inhibitory concentration values ranging between 7.8–62.4 µg mL−1. Further, some of the betaines also showed good anti-biofilm activity with IC50 values ranging between 2.1–25.3 µg mL−1 on the tested pathogenic microbial and fungal strains.


11-Bromoundecanoic acid Esterquats Betaines Antimicrobial activity Anti-biofilm activity 



One of the authors Sathyam Reddy gratefully acknowledges the Department of Biotechnology (DBT), New Delhi for the financial assistance under sponsored project and the Director, CSIR-IICT for providing the facilities.

Supplementary material

44_2017_1958_MOESM1_ESM.doc (546 kb)
Supplementary Information


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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • Sathyam Reddy Yasa
    • 1
  • Y. Poornachandra
    • 2
  • C. Ganesh Kumar
    • 2
  • Vijayalakshmi Penumarthy
    • 1
  1. 1.Centre for Lipid ResearchCSIR-Indian Institute of Chemical TechnologyHyderabadIndia
  2. 2.Medicinal Chemistry and Pharmacology DivisionCSIR-Indian Institute of Chemical TechnologyHyderabadIndia

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