Potential Nitrogen-Based Heterocyclic Compounds for Treating Infectious Diseases: A Literature Review

Abstract

Heterocyclic compounds are considered as one of the major and most diverse family of organic compounds. Nowadays, the demand for these compounds is increasing day-by-day due to their enormous synthetic and biological applications. These heterocyclic compounds have unique antibacterial activity against various Gram-positive and Gram-negative bacterial strains. This review covers the antibacterial activity of different heterocyclic compounds with nitrogen moiety. Some of the derivatives of these compounds show excellent antibacterial activity, while others show reasonable activity against bacterial strains. This review paper aims to bring and discuss the detailed information on the antibacterial activity of various nitrogen-based heterocyclic compounds. It will be helpful for the future evolution of diseases to synthesize new and effective drug molecules.

Keywords: heterocyclic compound; in-vitro studies; infectious disease; medicinal chemistry; organic synthesis.

Figure 1

Literature survey of antibacterial activity of nitrogen-based heterocyclic compounds.

Scheme 1

Synthetic route of pyrrole and its derivatives (4–27).

Scheme 2

Synthetic route for the synthesis of pyrrole[3,4-b]quinolin-2(3H)-yl)bezamide derivatives (37–41).

Scheme 3

Synthetic route of compound 44.

Scheme 4

Synthesis of pyrrole from 1,4-dicarbonyls.

Scheme 5

Synthesis of bis-pyrrole derivatives.

Scheme 6

Synthesis of 2H-chromene fused pyrrole derivatives (64–76).

Scheme 7

Synthetic route of pyrimidine from aromatic aldehyde (82–90).

Scheme 8

Synthesis of pyrimidine derivatives of 1,5-benzodiazepine from benzoylacetonitrile.

Scheme 9

Synthesis of new benzo[5,6]chromeno[2,3-d]pyrimidines (100–106).

Scheme 10

Synthesis of pyrimidine using acetamidine and isonicotinamidine.

Scheme 11

Synthesis of bis-pyrimidines (126–134).

Scheme 12

Synthesis of thieno[2,3-d]pyrimidine-alkyne.

Scheme 13

Synthesis of 3,4-dihydro-5-(5-mercapto-4H-1,2,4-triazol-3-yl)-6-methyl-4-phenyl pyrimidin-2(1H)-one (161–180).

Scheme 14

(Thiazol-2-yl)pyrazol-5-amines from pyrazolylthioureas and ω-bromoacetophenones.

Scheme 15

Synthetic route of compounds (192–209).

Scheme 16

Synthetic routes of various thiazoles.

Scheme 17

Synthetic routes of thiazole.

Scheme 18

Synthesis of thiazole from thiourea (253–256).

Scheme 19

Total synthesis of 4-thiazolylpyrazoles.

Scheme 20

Synthetic routes of substituted thiazole.

Scheme 21

The synthetic route to thiazole having pleuromutilin moiety.

Scheme 22

Synthesis of di-substituted pyridine (287–306).

Scheme 23

Synthesis of 6,8-dichloro-2-methylimidazo[1,2-a]pyridinyl-pyridine hybrids.

Scheme 24

Synthesis of fused heterocyclic compounds (Pyridine).

Scheme 25

Synthetic route of pyridine from urea derivatives.

Scheme 26

Synthesis of 3-amino-6-(trifluoromethyl)-1H-pyrazolo[3,4-b] pyridine-5-carboxylate.

Scheme 27

Synthesis of formyl pyridine. a = AcONH₄/EtOH.

Scheme 28

Synthesis of arylmethylene-isoxazol-5(4H)-one derivatives. a = LiBr/EtOH.

Scheme 29

Synthetic route of oxazole from hydroxyl aniline. a = CS₂/KOH/Reflux, b = Propargylbromide/K₂CO₃/m-CPBA/ArN₃/CuI/[Bmim]PF₆.

Scheme 30

Synthesis of 1,2-oxazoles 364–369.

Scheme 31

Synthetic route of compounds 374–376.

Scheme 32

Synthetic route of oxazole (379).

Scheme 33

Synthetic route of compounds (383–385).

Scheme 34

Synthesis of benzothiazole and benzoxazole linked 1,4-disubstituted 1,2,3-triazoles.

Scheme 35

Synthesis of 3-(2-aminooxazol-5-yl)-2H-chromen-2-one derivatives (414–426).

Scheme 36

Synthesis of sulfonamide bearing thiazolidinone (430–445).

Scheme 37

Synthesis of substituted 2-phenyl-3-(2-(trifluoromethyl)-1H-benzimidazol-6-yl)thiazolidin-4-ones.

Scheme 38

Synthesis of 2-(9-chloro-2,3-dimethyl- 6,7-dihydro-5H-benzo[7] annulen-8-yl)-3-(3-oxo-3-[piperazin-1-yl]propyl)thiazolidin-4-one derivatives.

Scheme 39

Synthetic pathways for compounds (477–486).

Scheme 40

Synthesis of thiazolidinone from benzylalcohol.

Scheme 41

Synthesis of thiazolidinone from benzoic acid (497–506).

Scheme 42

Synthesis of imidazole from diamine.

Scheme 43

Synthesis of imidazole-based 1,4-naphthoquinone.

Scheme 44

Synthesis of 5-methyl-2-(2-methyl-4,5-diphenyl-1H-imidazol-1-yl)phenol, 2-[2-(furan-2-yl)-4,5-diphenyl-1H-imidazol-1-yl]-5- methylphenol and 5-methyl-2-(2, 4, 5-triphenyl-1H-imidazole-1-yl) phenol.