Synthesis of novel non-isoprenoid phenolic acids and 3-alkylpyridines

Subhash C. Jain, Rohtash Kumar, Rajeev Goswami, Mukesh Pandey, Shilpi Khurana, Leena Rohatgi, Kapil Gyanda

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A new strategy has been developed for the synthesis of naturally occurring 6-alkenyl phenolic acids and 3-alkylpyridine alkaloids of biological importance. This strategy makes use of the proper substituted aryl or pyridyl sulfone as the potent intermediate. A carbanion was generated from the sulfone by treating it with NaH in dimethylformamide (DMF) at -5 °C and was used for alkylation reaction with alkyl/alkenyl bromide in DMF at 0 °C to give product, which, on reduction with sodium-amalgam, yielded the desired natural product. Using this methodology, we have synthesized 11 natural 6-alkyl/alkenyl salicylic acids, which were known to possess strong antimicrobial activities against many pathogens and had also shown molluscicidal activity against the snail Biomphalaria glabrata. This methodology was also extended to synthesize two natural 3-alkylpyridine alkaloids that were known to possess strong cytotoxic activity against P-388 murine leukemia cells with IC50 values of 1-2.3 μg/ml. Taking leads from these natural products, we have also synthesized a number of related compounds in order to find a potential drug candidate for the future. This paper presents the highlights of the work done on the synthesis of these two classes of compounds.

Original languageEnglish (US)
Pages (from-to)185-193
Number of pages9
JournalPure and Applied Chemistry
Volume77
Issue number1
DOIs
StatePublished - Jan 1 2005
Externally publishedYes

Fingerprint

Alkaloids
Dimethylformamide
Sulfones
Biological Products
Salicylic acid
Mercury amalgams
Acids
Salicylates
Alkylation
Pathogens
Bromides
Sodium
Pharmaceutical Preparations
phenolic acid

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Jain, S. C., Kumar, R., Goswami, R., Pandey, M., Khurana, S., Rohatgi, L., & Gyanda, K. (2005). Synthesis of novel non-isoprenoid phenolic acids and 3-alkylpyridines. Pure and Applied Chemistry, 77(1), 185-193. https://doi.org/10.1351/pac200577010185

Synthesis of novel non-isoprenoid phenolic acids and 3-alkylpyridines. / Jain, Subhash C.; Kumar, Rohtash; Goswami, Rajeev; Pandey, Mukesh; Khurana, Shilpi; Rohatgi, Leena; Gyanda, Kapil.

In: Pure and Applied Chemistry, Vol. 77, No. 1, 01.01.2005, p. 185-193.

Research output: Contribution to journalArticle

Jain, SC, Kumar, R, Goswami, R, Pandey, M, Khurana, S, Rohatgi, L & Gyanda, K 2005, 'Synthesis of novel non-isoprenoid phenolic acids and 3-alkylpyridines', Pure and Applied Chemistry, vol. 77, no. 1, pp. 185-193. https://doi.org/10.1351/pac200577010185
Jain, Subhash C. ; Kumar, Rohtash ; Goswami, Rajeev ; Pandey, Mukesh ; Khurana, Shilpi ; Rohatgi, Leena ; Gyanda, Kapil. / Synthesis of novel non-isoprenoid phenolic acids and 3-alkylpyridines. In: Pure and Applied Chemistry. 2005 ; Vol. 77, No. 1. pp. 185-193.
@article{0bb58d328ba742719a425b0fe1944e7f,
title = "Synthesis of novel non-isoprenoid phenolic acids and 3-alkylpyridines",
abstract = "A new strategy has been developed for the synthesis of naturally occurring 6-alkenyl phenolic acids and 3-alkylpyridine alkaloids of biological importance. This strategy makes use of the proper substituted aryl or pyridyl sulfone as the potent intermediate. A carbanion was generated from the sulfone by treating it with NaH in dimethylformamide (DMF) at -5 °C and was used for alkylation reaction with alkyl/alkenyl bromide in DMF at 0 °C to give product, which, on reduction with sodium-amalgam, yielded the desired natural product. Using this methodology, we have synthesized 11 natural 6-alkyl/alkenyl salicylic acids, which were known to possess strong antimicrobial activities against many pathogens and had also shown molluscicidal activity against the snail Biomphalaria glabrata. This methodology was also extended to synthesize two natural 3-alkylpyridine alkaloids that were known to possess strong cytotoxic activity against P-388 murine leukemia cells with IC50 values of 1-2.3 μg/ml. Taking leads from these natural products, we have also synthesized a number of related compounds in order to find a potential drug candidate for the future. This paper presents the highlights of the work done on the synthesis of these two classes of compounds.",
author = "Jain, {Subhash C.} and Rohtash Kumar and Rajeev Goswami and Mukesh Pandey and Shilpi Khurana and Leena Rohatgi and Kapil Gyanda",
year = "2005",
month = "1",
day = "1",
doi = "10.1351/pac200577010185",
language = "English (US)",
volume = "77",
pages = "185--193",
journal = "Pure and Applied Chemistry",
issn = "0033-4545",
publisher = "IUPAC Secretariat",
number = "1",

}

TY - JOUR

T1 - Synthesis of novel non-isoprenoid phenolic acids and 3-alkylpyridines

AU - Jain, Subhash C.

AU - Kumar, Rohtash

AU - Goswami, Rajeev

AU - Pandey, Mukesh

AU - Khurana, Shilpi

AU - Rohatgi, Leena

AU - Gyanda, Kapil

PY - 2005/1/1

Y1 - 2005/1/1

N2 - A new strategy has been developed for the synthesis of naturally occurring 6-alkenyl phenolic acids and 3-alkylpyridine alkaloids of biological importance. This strategy makes use of the proper substituted aryl or pyridyl sulfone as the potent intermediate. A carbanion was generated from the sulfone by treating it with NaH in dimethylformamide (DMF) at -5 °C and was used for alkylation reaction with alkyl/alkenyl bromide in DMF at 0 °C to give product, which, on reduction with sodium-amalgam, yielded the desired natural product. Using this methodology, we have synthesized 11 natural 6-alkyl/alkenyl salicylic acids, which were known to possess strong antimicrobial activities against many pathogens and had also shown molluscicidal activity against the snail Biomphalaria glabrata. This methodology was also extended to synthesize two natural 3-alkylpyridine alkaloids that were known to possess strong cytotoxic activity against P-388 murine leukemia cells with IC50 values of 1-2.3 μg/ml. Taking leads from these natural products, we have also synthesized a number of related compounds in order to find a potential drug candidate for the future. This paper presents the highlights of the work done on the synthesis of these two classes of compounds.

AB - A new strategy has been developed for the synthesis of naturally occurring 6-alkenyl phenolic acids and 3-alkylpyridine alkaloids of biological importance. This strategy makes use of the proper substituted aryl or pyridyl sulfone as the potent intermediate. A carbanion was generated from the sulfone by treating it with NaH in dimethylformamide (DMF) at -5 °C and was used for alkylation reaction with alkyl/alkenyl bromide in DMF at 0 °C to give product, which, on reduction with sodium-amalgam, yielded the desired natural product. Using this methodology, we have synthesized 11 natural 6-alkyl/alkenyl salicylic acids, which were known to possess strong antimicrobial activities against many pathogens and had also shown molluscicidal activity against the snail Biomphalaria glabrata. This methodology was also extended to synthesize two natural 3-alkylpyridine alkaloids that were known to possess strong cytotoxic activity against P-388 murine leukemia cells with IC50 values of 1-2.3 μg/ml. Taking leads from these natural products, we have also synthesized a number of related compounds in order to find a potential drug candidate for the future. This paper presents the highlights of the work done on the synthesis of these two classes of compounds.

UR - http://www.scopus.com/inward/record.url?scp=14644401755&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=14644401755&partnerID=8YFLogxK

U2 - 10.1351/pac200577010185

DO - 10.1351/pac200577010185

M3 - Article

AN - SCOPUS:14644401755

VL - 77

SP - 185

EP - 193

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

SN - 0033-4545

IS - 1

ER -