Pyridine and Its Biological Activity: A Review

 

Prathima Patil*, S.P. Sethy, T. Sameena, K. Shailaja

Department of Medicinal Chemistry, Sushrut Institute of Pharmacy,

Tadanpally (v), Pulkal(m), Medak Dist-754202

*Corresponding Author E-mail: pratima.patil0@gmail.com

 

Pyridine is a planer Six-member heterocyclic ring with 5C and 1N atom and in ring N is present in 1^st and positions. The Pyridine ring is a constituent of several important natural products, including niconine, nicotine, and nucleic acid. Being a polar and ionisable aromatic compound, it improves pharmacokinetic characteristics of lead molecules and thus used as a remedy to optimize solubility and bioavailability parameters of proposed poorly soluble lead molecules. Pyridine derivatives have occupied a unique place in the field of medicinal chemistry. The incorporation of the pyridine nucleus is an important synthetic strategy in drug discovery. The high therapeutic properties of the Pyridine related drugs have encouraged the medicinal chemists to synthesize a larger number of novel chemotherapeutic agents. Pyridine drugs have broadened scope in remedying various dispositions in Clinical medicines. Numerous methods for the synthesis of Pyridine and also their various structure reactions offer enormous scope in the field of medicinal chemistry. This articles aims to review the work reported, their chemistry and biological activities of Pyridine during past years.

 

 

INTRODUCTION:

Medicinal chemistry is the discipline concerned with determing the influence of chemical structure on biological activity and in the practice of medicinal chemistry developed from an empirical one involving organic synthesis of new compound based largely on the modification of structure and then identifies their biological activity. Medicinal chemistry concerns with the discovery, development, interpretation and the identification of mechanism of action of biologically active compounds at the molecular level. Various biologically active synthetic compounds have Six-membered nitrogen containing heterocyclic ring in their structures. Structural frameworks have been described as privileged structures and in particular, N containing polycyclic structures has been reported to be associated with a wide range of biological activity. In the field of six membered heterocyclic structures Pyridine nucleus shows various properties. The high therapeutic properties of the Pyridine related drugs have encouraged the medicinal chemists to synthesize a large number of novel chemotherapeutic agents.

 

Pyridine drugs have broadened scope in remedying various dispositions in clinical medicines. Medicinal properties of Pyridine include anti hypertensive, anti histaminics, anticoagulants, anti-inflammatory, antibacterial, antifungal, antiviral, ant tubercular, ant diabetic and ant malarial. Some Pyridine drugs, at high concentrations, could exert direct inhibitory action on membranes, without interference with sterols and sterol esters. Infectious microbial disease causes worldwide problem, because microbes have resisted prophylaxis or therapy longer than any other form of life. In recent decades, problems of multidrug-resistant microorganisms have reached an alarming level in many countries around the world. Resistance of anti-microbial agents such as β-lactam antibiotics, macrolides, quinolones and vancomycin etc. and different species of bacteria causes increased important global problem. Pyridine and its derivatives are reported to be physiologically and pharmacologically active and find applications in the treatment of several diseases.

 

Structure and pharmacological activities:

Pyridines are well known heterocyclic compounds which are common and have important feature of a variety of medicinal agents. Pyridine is a 6-membered planar ring, which is soluble in water and other polar solvents. It exists in two equivalent tautomeric forms because the hydrogen atom can be located on either of the two nitrogen atoms. It is a highly polar compound, as evidenced by a calculated dipole of 3.61D, and is entirely soluble in water. The compound is classified as aromatic due to the presence of a sextet of -electrons, consisting of a pair of electrons from the protonated nitrogen atom and one from each of the remaining four atoms of the ring. Imidazole is amphoteric, i.e. it can function as both an acid and as a base. On the basis of various literature surveys Imidazole derivatives shows various pharmacological activities

 

·         Anti-hypertensive

·         Anti-bacterial

·         Anti psychotic

·         Skeletal Muscle Relaxant

·         Analgesic

·         MAO-Inhibition

·         CNS Stimulant

·          Sedative

·         Anti Depressant

·         Anti- Cholinergic

 

 

Table: imidazole ring containing few marketed drug shows various biological activitie

STRUCTURE	USES		REFERENCES
1.Nifedipine   dimethyl2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate	It is a first generation calcium channel blocker having peripheral and coronary artery dilating properties. It is used in the treatment of angina and hypertension.		Pandya.SN.et.al[1]
2.Amlodipine   (RS)-3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate	It is used as an antihypertensive  in the treatment of angina pectoris		Wang.JG.et.al[2]
3.Nivaldipine   methyl propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate	Nilvadipine is a calcium channel blocker (CCB) used for the treatment of hypertension and chronic major cerebral artery occlusion		Pandya.SN.et..al[3]
4.Sulfasalazine   2-hydroxy-5-{(Z)-[4-(pyridin-2-ylsulfamoyl)phenyl]diazenyl}benzoic acid	It is specifically used to treat rheumatoid arthritis		McGirt LY.et.al[4]
5.Norfloxacine   4-(diethylamino)-7-fluoro-1-oxo-6-(piperazin-1-yl)-1,4-dihydronaphthalene-2-carboxylic acid	Norfloxacin is a synthetic anti bacterial agent used for the treatment of urinary tract infection		Rafalsky.V.et.al[5]
6.Zolpidem   2-[2-(4-methylphenyl) imidazo [1,2-a]pyridin-3-yl]acetamide	It is used for the treatment of insomnia and some brain disorders		Lemmer B.et.al[6]
7.Bromazepame   7-bromo-5-(pyridin-2-yl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one	It has mainly anxiolytic  properties and at higher doses of 12 milligrams or more also shows sedative, hypnotic and skeletal muscle relaxant properties		Guelfi JD.et.al[7]
8.Flupirtine   ethyl {2-amino-6-[(4-fluorobenzyl)amino]pyridin-3-yl}carbamate	It acts as a centrally acting non-opioid analgesic		SwedbergMD.et.al[8]
9.Harmine   1-(1-methyl-9H--carbolin-7-yl)ethanone	It is a alkaloid having reversible MAO inhibitory properties		Pandya.SN.et.al[9]
10.Nikthimide   N,N-diethylpyridine-3-carboxamide	It is used s a CNS stimulant and respiratory stimulant		Martindale.et.al[10]
11.Pyrilamine   N-(3-methoxybenzyl)-N',N'-dimethyl-N-(pyridin-2-yl)ethane-1,2-diamine	It is used in over-the-counter combination products to treat the common cold and menstrual symptoms		Parsons.et.al[11]
12.Methapyriline   N,N-dimethyl-N'-(pyridin-2-yl)-N'-(thiophen-2-ylmethyl)ethane-1,2-diamine	it is an antihistamine  and anti-cholinergic of the pyridine chemical class used for sedation		Pandya.SN.et.al[12]
13.Doxylamine   N,N-dimethyl-2-[1-(pyridin-2-yl)ethoxy]ethanamine	It can be used by itself as a short-term sedative and in combination with other drugs to provide night-time allergy and cold relief		Briggs GG.et.al[13]
14. Chlorphenamine   4-(4-chlorophenyl)-N,N-dimethyl-4-(pyridin-2-yl)butan-1-amine	Chlorphenamine is one of the most commonly used antihistamines in small-animal veterinary practice. Although not generally approved  As an antidepressant or anti-anxiety medication,		Carlsson.A.et.al[14]
15.Triprolidine   2-[1-(3-chlorophenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridine	It is used to combat the symptoms associated withallergies and is sometimes combined with other cold medications designed to provide general relief for flu-like symptoms.		Pandya.s.n.et.al[15]
16.Azatadine   6,11-Dihydro-11-(1-methyl-4-piperidine)-5H-benzo[5,6] cyclohepta[1,2,-b] pyridin	Azatadine is an antihistamine and  anticholinergic drug.		Zhang D.et.al[16]
17.Acrivastine   (2E)-3-{6-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridin-2-yl}prop-2-enoic acid	Acrivastine is a medication used for the treatment of allergies and hay fever		Pandya.SN.et.al[17]
18.Loratidine   ethyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate	Loratadine is a second-generation H1 histamine antagonist drug used to treat allergies		Holdcroft.C.et.al[18]
19.Rocastine   2-[2-(dimethylamino)ethyl]-4-methyl-3,4-dihydropyrido[3,2-f][1,4]oxazepine-5(2H)-thione	It is a rapid acting, non-sedating antihistamine		Nolan JC, et.al[19]
20.Cicletamide   6-methyl-3-(4-methylphenyl)-1,3-dihydrofuro[3,4-c]pyridin-7-ol	H1 receptor antagonist		Pandya.SN.et.al[20]
21.Lupitidine   2-({2-[({5-[(dimethylamino)methyl]furan-2-yl}methyl)sulfanyl] ethyl} amino)-5-[(6-methylpyridin-3-yl)methyl]pyrimidin-4(3H)-one	Lupitidine is an H2 receptor antagonist described as an antiulcer agent		Pandya.SN.et.al[21]
22.Omeprazole   1-(2-{[(4,5-dimethoxy-3-methylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazol-6-yl)ethanone	It is a proton pump inhibitorused in the treatment of dyspepsia, peptic ulcerdisease (PUD),  gastroesophageal reflux disease (GORD/GERD),  laryngopharyngeal reflux (LPR) and Zollinger–Ellison syndrome.		Ang YX.et.al[22]
23.Disopyramide Phosphate   S)-4-(diisopropylamino)-2-phenyl-2-(pyridin-2-yl)butanamide	It is an ant arrhythmic medication used in the treatment of Ventricular Tachycardia		Guyton.et.al[23]
24.Nitrendipine   (RS)-ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate	It is used in the treatment ofprimary (essential) hypertension to decrease blood pressure.		Asif A.et.al[24]
25.Felodipine   5-ethyl 3-methyl 4-(2,3- dichlorophenyl)-2-formyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate	It is a drug used to control hypertension (high blood pressure)		Pandya.SN.et.al[25]
26.Lacidipine   5-diethyl 4-{2-[(1E)-3-(tert-butoxy)-3-oxoprop-1-en-1-yl]phenyl}-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate	It is  a calcium channel blocke		Pandya.SN.et.al[26]
27.Nicorandil   hydroxy(oxo){2-[(pyridin-4-ylcarbonyl)amino]ethoxy}ammonium	It is a vasodilator  drug used to treat angina		Tripathi.K.D.et.al[27]
28.Amrinone   5-amino-3,4'-bipyridin-6(1H)-one	It is is a pyridine  phosphodiesterase 3 inhibitor. It is a drug that may improve the prognosis in patients with congestive heart failure		Klein N.A.et.al[28]
29.Sulmazole   2-[2-methoxy-4-(methoxysulfanyl)phenyl]-3H-imidazo[4,5-b] pyridin	It is used In the treatment of congestive heart failure		Pandya.SN.et.al[29]
30.Nicotinamid   N-methylbenzamide	It is used for type-iii  hyperliporotemia		Knip M.et.al[30]
31.Pyridostigmine   1,6-dihydropyridin-3-yl dimethylcarbamate	It is used in the treatment of myasthenia gravis		Pandya.SN.et.al[31]
32.Nicotine   3-(1-methylpyrrolidin-2-yl)pyridin	It is use of nicotine is in treating nicotine dependence in order to eliminate smoking		Thomas GA.et.al[32]
33.Tropicamide   N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide	It is used in Myasthenia graves and cycloplegia		Manny RE.et.al[33]
34.Piperazine     11-[(4-methylpiperazin-1-yl)acetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one	It has been used in the treatment of ulcer		Tolerman.et.al[34]
35.Naidixic acid   1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid.	It is used in the urinary tract infection	Pandya.SN.et.al[35]
36.Enoxacin   1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid	It is used in the treatment of respiratory tract infection and urinary tract infection	Mogabgab.WJ.et.al[36]
37.Phenazopyridie HCl   3-[(Z)-phenyldiazenyl]pyridine-2,6-diamine hydrochloride	It is used as an analgesic in urinary tat infection and dysuria	Thomas BH.et.al[37]
38. Cetylpyrdiiucloride   1-Hexadecylpyridinium chloride	It is an antiseptic that kills bacteria and other microorganisms	Asadoorian.et.al[38]
39.Isoniazide   pyridine-4-carbohydrazide	It is the first-line medication in prevention and treatment of tuberculosis	Jones.et.al[39]
40.Etioamide   2-ethylpyridine-4-carbothioamide	It is an antibiotic used in the treatment of tuberculosis	Vannelli TA.et.al [40]
41.Enpirolin   (R)-(2R)-piperidin-2-yl{2-(trifluoromethyl)-6-[4-(trifluoromethyl)phenyl]pyridin-4-yl}methanol	It is used as a ant malarial drugs	Pandya.SN.et.al[41]
42.Delaveridine   N-[2-({4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl}carbonyl)-1H-indol-5-yl]methanesulfonamide	It is used as part of highly active antiretroviral therapy (HAART) for the treatment of human immunodeficiency virus	Pandya.SN.et.al[42]
43.Nevirapine   11-cyclopropyl-4-methyl-5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	It is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used to treat HIV-1infection and AIDS	Patel SS.et.al[43]
44.Indinavir   2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide	It is a protease inhibitor used as a component of highly active antiretroviral therapy (HAART) to treat HIV infection and AIDS	Liu, F.et.al[44]
45.Dipyridodiazpine   11-cyclopropyl-4-methyl-5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one	It is used for both IV-1 and HIV-II Infection	Pandya, SN.et.al[45]
46.Ciclopirox olamine   6-cyclohexyl-4-methylpyridin-2(1H)-one	It is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses	Niewerth M.et.al[46]
47.Cephapirine   3-[(acetyloxy)methyl]-8-oxo-7-{[(pyridin-4-yldisulfanyl)carbonyl]amino}-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	It is an inject able, first-generation  cephalosporin antibiotic	Pandya, SN.et.al[47]
48.Iodoxyl   propyl (3,5-diiodo-4-oxopyridin-1(4H)-yl)acetate	It is used as a diagnostic agent in kidney and uterus	Pandya, SN.et.al[48]
49.Propylidone   propyl (3,5-diiodo-4-oxopyridin-1(4H)-yl)acetate	It is used in fistula, sinus and bronchography	Pandya, SN.et.al[49]
50.Metyrapone   2-methyl-1,2-di(pyridin-3-yl)propan-1-one	It is a drug used in the diagnosis of adrenal insufficiency and occasionally in the treatment of Cushing's syndrome	Marin.et.al[50]
51.Abiraterone   (3β)-17-(pyridin-3-yl)androsta-5,16-dien-3-ol	It is a drug used in castration-resistant prostate cancer	O'Donnell A.et.al[51]

 

 

CONCLUSON:

The reviewed pyridine moiety has shown a wide spectrum of biological activities. The various substituted pyridine and are having significant antifungal activity. Significant, antiviral and anti asthmatic activity is displayed by some effective substituted pyridine derivative which presently leading drug in the market in entire. some modified pyridine  are found to to be effective as anti-hypertensive, whereas some of the derivatives of pyridine are found to show the anti-asthmatic, anti;viral as special anti HIV action. Recently it was proven that, some of the important marketed pyridine nucleous containing drug having different biological or pharmacological activity were discussed in table. The pyridine  nucleolus based pharmaceutical are rapidly becoming very important class of therapeutic agents and are likely to replace many existing organic based pharmaceuticals in the very near future. The pyridine based pharmaceuticals will be produced on a large scale by modern drug Discovery Company by different research development processes and will become available commercially for therapeutic use. With the key benefits including favorable time to market and high rate of success in clinical trial compared with traditional pharmaceuticals due to diverse biological action with less toxicity, so in future therapeutic indole drug will play a pivotal role in the treatment of different diseases. The biological profiles of this new generation of pyridine represent much progress with regard to the older compounds.

 

 

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Received on 04.08.2013          Modified on 19.08.2013

Accepted on 23.08.2013         © AJRC All right reserved