Int J Curr Pharm Res, Vol 15, Issue 1, 15-18Review Article


BIOLOGICAL ACTIVITY OF QUINAZOLINONE DERIVATIVES: A REVIEW

WAGHMARE SWEETI M., MANCHARE AKANKSHA M.*, SHAIKH AVESH Y.*, DIKSHA RAUT G.*

Department of Pharmaceutical Chemistry, Shantiniketan College of Pharmacy, Dhotre (BK), Ahmednagar 414304
Email: waghmaresweeti11@gmail.com

Received: 15 Oct 2022, Revised and Accepted: 22 Dec 2022

ABSTRACT

The heterocyclic compounds have a great importance in medicinal chemistry. Quinazolinone is a heterocyclic chemical compound. A quinazolinone with a carbonyl group in the C4N2 ring. The two isomers are possible: 2-Quinazolinone and 4-Quinazolinone, with the 4-isomer being the more common. These compounds are of interest in medicinal chemistry. Quinazolinone derivatives were reported to possess analgesic and anti-inflammatory activity, Antibacterial, Diuretic, Antihypertensive, Anti-diabetics, Anticancer, Antitumor, Anti-fungal, Anti-malarial, Anti-protozoal agent and many other biological Action. This skeleton is an important pharmacophore considered as a privileged structure.

Keywords: Quinazolinone, Antibacterial, Diuretic, Antifungal, Antitumor, Anticancer, Anti-diabetics, Antihypertensive, Anti-malarial

© 2023 The Authors. Published by Innovare Academic Sciences Pvt Ltd. This is an open access article under the CC BY license (https://creativecommons.org/licenses/by/4.0/)
DOI: https://dx.doi.org/10.22159/ijcpr.2023v15i1.2074 Journal homepage: https://innovareacademics.in/journals/index.php/ijcpr

INTRODUCTION

Quinazolinone are the class of heterocycles that are of considerable interest because of diverse range of their biological properties [1]. Quinazolinone will be classified into following five categoriers based on their substitution partition of the ring system.

There are 2 substituted-4(3H)-quinazolinone, 3substituted-4(3H)-quinazolinone, 4substituted quinazolinone,2,3-disubstituted-4-(3H)quinazolinone, 2,4-disubstituted-4-(3H) quinazolinone [2]. Quinazolinone derivative passes a wide range of bioavtivities, Antibacterial, Diuretic, Antihypertensive, Antidiabetics, Anticancer, Antitumor, Anti fungal, Anti malerial, Anti protozamol agent and many other biological Action [3]. For medical preparation as, the natural and synthetic origins of quinazolinone 4 derivative Quinazolinone derivative are reported to be physiological and pharmaceutical Action [4].

Osol A. and J. E hoover studies on 2 substituted 7-chloro-2ethyl-4-oxo-1,2,3,4-tetrahydroquinazoline and check antihypertensive activity. This compound shows maximum activity used as reference drug [5].

Fig. 1: 7-chloro-2ethyl-4-oxo-1,2,3,4-tetrahydroquinazoline

Molecular formula: C10H12CIN3NO3S

Molecular weight: 289.73 gm/mol

Common name: Quinethazone.

Melting point: 482–486 °F

Properties: It is oral drug administration. It is White to yellowish white crystalline powder [5]. It is odourless Bitter taste.

Solubility: Less than 1 mg/ml at 67.1 °F Soluble in acetone and Alcohol but slightly soluble in water [6].

Pharmacological action: Quinethazone solid under the brand name hydromox. It is a Thiazide like diuretic used to treat hypertension [7]. Common side effect are Dizziness, Dry mouth, nausea, and low potassium level.

B. Vijayakumar, P. Prasanthi, K. M. Teja et al. studies on 3 substituted 7-chloro-4-oxo-2phenyl 2,3 dihydro 1H quinazoline-6-sulphonamide and checkthe antihypertensive and diuretic activity. This compound show maximum activity used as a reference [8].

Fig. 2: 7-chloro-4-oxo-2phenyl2,3dihydro1Hquinazoline-6 sulphonamide

Molecular formula: C14H12CLN3O3S

Molecular Weight: 337.8 gm

Common name: Fenquizone.

Melting Point: 72.96 °C

Properties: Fenquizone is member of quinazolinone entities of biologicalinterest.

Phaemacological action: It is diuretics part of the class of low celling sulphonamide. Diuretics [8]. Fenquizone is used primary in the treatment of hypertension [9].

B. Vijayakumar, P. Prasanthi, K. M. Teja et al. studied on 5 substituted 5-Fluro-3phenyl-2-[(1s)-1-(7H)-purin-6-ylaminol propyl]-4(3H)-quinazolinone and check the anti-cancer activity. This compound shows maximum activity and used as a referenc [12].

Fig. 3: 5-Fluro-3phenyl-2-[(1s)-1-(7H)-purin-6-ylaminolpropyl]-4(3H) quinazolinone

Molecular formula: C22H18FN7O

Molecular weight: 415–432 gm/mol

Common name: Idelalisib.

Melting Point: 250-252 °C

Properties: It is white to off-white powder,with pH-dependent aqeous solubility ranging.

Solubility: Soluble in water [10] sparingly soluble in ethanol [11].

Pharmacological action: Idelalisib sold under the brand name zydelig is medication used the certain blood cancer [12]. It treat different type of leukemia [13].

V. K. Srivastava and A. Kumar, studies on 5 substituted-[(4-(3-methyl-4-oxoquinazolin-2-yl)methoxy)phenyl]-1,3 thiazolidine-2,4dioneand check the anti diabetic activity. This compound show maximum activity on used as a reference drug [14].

Fig. 4:5-[(4-(3-methyl-4-oxoquinazolin-2-yl)methoxy)phenyl]-1,3 thiazolidine-2,4dione

Molecular Formula: C20H17N3O4S

Molecular weight: 395.4 gm/mol.

Common name: Balaglitazone.

Properties: It is second generation peroxisomes proliferates receptor gamma agonist with only partical agonistic properties.

Pharmacological action: It has been used in trails studing the treatment of diabetes mellitus. Type 2 blood glucose lowering agent.

W. L. Armarego studies on 2 methyl-3-otolyl-4(3H)-quinazolinone and check the activity of sedative and hypnotic. This compound show maximum activity and used as a reference drug [16].

Fig. 5:2 methyl-3-otolyl-4(3H)-quinazolinone

Molecular Formula: C16H14N2O

Molecular weight: 250.30 gm/mol.

Common name: Methaqualone

Melting Point: 113 °C

Properties: Crystals white or almost white crystalline powder, no odour,bitter taste [14].

Solubility: Soluble in alcohol, chloroform and ether but insoluble in water [15].

Pharmacological action: It is used in the treatment of insomnia and as sedative and hypnotics it increases GABA Action.

K. C. Agarwal, V. Sharma, N. Shakya, and S. Guptastudied on 3 substituted (2,3-dihydroxypropyl)-2-methyl-quinazolin-4-one and check the anti-inflammatory activity. This compound shows maximum activity and used as reference drug [17].

Fig. 6: 3-(2,3-dihydroxypropyl)-2-methyl-quinazolin-4-one

Molecular Formula: C12H14N2O3

Molecular weight: 234-251 gm/mol

Common name: Diproqualone.

Properties: It is quinazolinone class and analogue of methaqualone developed in late 1950’s by a team at nogenataise de product chimique

Pharmacological action: It has sedative, anxiolytic, antihistamine and analgesic properties It is used primarily for the treatment of inflammation [16].

D. Kohli, S. R. Hashim, S. Vishal, M. Sharma, and A. K. Singhstudied on 3 substituted (2,6-diclorophenyl)-2-ethyl-4-quinazolinone and check anti-tissue activity. This compound shows maximum activity [18].

Fig. 7: 3-(2,6-diclorophenyl)-2-ethyl-4-quinazolinone

Molecular formula: C16H12CL2N2O

Molecular weight: 319.185 gm/mol

Common name: choloroqualone

Properties: choloroqualone has weaker sedative properties than methaqualone it has sold either alone or in combination with other ingredients as cough medicine.

Pharmacological action: It shows sedative and Antitissue properties resulting from agonist Action. It useful in the cough-suppressing effect [17].

A. Omar, M. F. Fattah, M. M. Emad, M. I. Neama, and M. K. Mohsen, studied 3 substituted 7-Bromo-6choro-3-[3-[(2S,3R)-3-hydroxy-2piperadinyl]-2oxopropyl]4-quinaxoline and check anti-inflammatory activity [19].

Fig. 8: 7-Bromo-6-chloro-3-[3-[(2S,3R)-3-hydroxy-2-piperadinyl]2oxopropyl]4-quinaxoline

Molecular formula: C16H17BrCLN3O3

Molecular weight: 414.68 gm/mol

Common name: Halofuginane

Melting point: 105 °C

Properties: A potent inhibiter of collagen alpha 1 and matrix metalloproteinase 2 gene expression

Solubility: soluble in water

Pharmacological action: It is used in veterinary medicine Halofuginone, therefore, has the potential for the treatment of an autoimmune disorder. It is also used for anti-inflammatory and anti fibrotic effect.

A. Gürsoy and N. Terzioğlustudied on 3 substituted {3-[(2R,3S)-3-hydroxypiperidin-2yl]-2-oxopropyl}quinazaline-4(3H)-one and check the anti-material, anticancer and anti-inflammatory activity. This compound shows maximum activity and used as a reference drug [20].

Fig. 9: 3-{3-[(2R,3S)-3hydroxypiperidin-2yl]-2-oxopropyl}quinazaline-4(3H)-one

Molecular formula: C16H19N3O3

Molecular weight: 301.346 gm/mol

Common name: febrifugine

Melting point: 139–140 °C

Solubility: Soluble in ethanol

Properties: Potent antimalarial Action; febrifugine is a natural product found in Hydrangedfebrifuga.

Pharmacological action: It is used as veterinary medicine and also used against malaria, cancer and inflammatory disease [18].

C. Balakumar, P. Lamba, D. Pran Kishore, studied on 3 substituted [(E)2-phenylethenyl]quinazolin-4-oneand check antiseptic activity. This compound shows maximum activity and used as a reference drug [21].

Fig. 10: 3-[(E)2-phenylethenyl]quinazolin-4-one

Molecular Formula: C16H12N2O

Molecular weight: 248.28 gm/mol

Common name: Bogorine

Melting point: 2076 °C

Solubility: slightly soluble in water

Properties: Amorphous dark brown to black powder brittle crystalline metal occur as a high-purity bogorine [19].

Pharmacological action: It is used in eye drops, mild anti-septic and also used in food preservative.

CONCLUSION

On the basis of various literature survey, Quinazolinone Derivatives shows various Pharmacological Action against Antibacterial, Anti septic, Anti-fungal, Anti-cancer, Anti-hypertensive and Anti-inflammatory agent. Various recent new drug developments in quinazolinone derivatives shows greater effect and less toxicity.

FUNDING

Nil

AUTHORS CONTRIBUTIONS

All the authors have contributed equally.

CONFLICT OF INTERESTS

Declared none

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