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IJCRR - 2(11), November, 2010

Pages: 14-26

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1,3,4-THIADIAZOLE AS ANTIINFLAMMATORY AGENT:A REVIEW

Author: Mehnaz Kamal, Ashok K Shakya, Talha Jawaid

Category: Healthcare

Abstract:1,3,4-Thiadiazole nucleus exhibited remarkable pharmacological activities. Literature indicates that compounds having 1,3,4-Thiadiazole nucleus have wide range of pharmacological activities that include antibacterial, antifungal, antitubercular, antiviral, antileishmanial, anti-inflammatory, analgesic, CNS depressant, anticonvulsant, anticancer, antioxidant, antidiabetic, molluscicidal, antihypertensive, diuretic. The present review provides a broad view of the anti-inflammatory activity possessed by compounds having a 1,3,4-Thiadiazole nucleus.

Keywords: Review; 1, 3, 4-Thiadiazole; Chemistry; anti-inflammatory Activity

Full Text:

Introduction

One of the main objectives of organic and medicinal chemistry is the design, synthesis and production of molecules having value as human therapeutic agents. During the past decade, combinatorial chemistry has provided access to chemical libraries based on privileged structures [1], with heterocyclic structures receiving special attention as they belong to a class of compounds with proven utility in medicinal chemistry [2]. There are numerous biologically active molecules with five membered rings, containing three hetero atoms. Thiadiazole is an important scaffold known to be associated with several biological activities (Fig.1.).

Chemistry of 1,3,4-Thiadiazole

Thiadiazole is a five membered heterocyclic compound. It contains two nitrogen atoms and one sulphur atom as hetero atoms. Thiadiazole may be of 1,2,3- thiadiazoles (a) ; 1,2,4- thiadiazole (b) ; 1,3,4-thiadiazole (c) and 1,3,5-thiadiazole (d).

Anti-inflammatory properties:

Nonsteroidal anti-inflammatory drugs (NSAIDs) are an inhomogeneous family of pharmacologically active compounds used in the treatment of acute and chronic inflammation, pain, and fever. The inhibition of prostaglandin E2 (PGE2) and nitric oxide (NO) production has been proposed as a potential therapy for different inflammatory disorders. Large amounts of NO may lead to tissue damage. In inflammatory diseases such as rheumatoid arthritis, excessive NO production by activated macrophages has been observed. Therefore, it would be interesting to develop potent and selective inhibitors of NO for potential therapeutic use.

Kumar et al.(2008) synthesized a series of 1,3,4-thiadiazole derivatives of biphenyl-4-yloxy acetic acid (1) in order to obtain new compounds with potential anti-inflammatory activity, analgesic activity and lower ulcerogenic potential. All compounds were evaluated for their anti-inflammatory activity by the carrageenan induced rat paw edema test method. The compounds possessing potent antiinflammatory activity were further tested for their analgesic, ulcerogenic and antioxidant activities. Some compounds showed significant reduction in rat paw edema induced by carrageenan treatment. These compounds showed significant analgesic effect and at an equimolar oral doses relative to flurbiprofen were also found to be non-gastrotoxic in rats [3]. Amir et al.(2007) synthesized some 6- substituted-1,2,4-triazolo[3,4-b]-1,3,4- thiadiazole derivatives (2-3). The compounds were pharmacologically evaluated for their anti-inflammatory and analgesic potentials by known experimental models. Several of these showed significant activity. Very low ulcerogenic index was observed for potent compounds [4]. Amir et al.(2007) prepared several 3,6- disubstituted-1,2,4-triazolo-[3,4-b]- 1,3,4-thiadiazoles (4-5). These compounds were investigated for their anti-inflammatory, analgesic, ulcerogenic, lipid peroxidation, antibacterial and antifungal activities. Some of the synthesized compounds showed potent anti-inflammatory activity along with minimal ulcerogenic effect and lipid peroxidation, compared to those of ibuprofen and flurbiprofen. Some of the tested compounds also showed moderate antimicrobial activity against tested bacterial and fungal strains [5]. Goksen et al.(2007) synthesized 1,3,4- thiadiazoles containing 5-methyl-2- benzoxazolinones (6). Most of the compounds were exhibiting high activity in analgesic-anti-inflammatory field [6]. Hafez et al.(2008) synthesized novel spiro-thioxanthene-9',2- [1,3,4]thiadiazoles and spiro-xanthene- 9',2-[1,3,4]thiadiazoles (7). The newly synthesized compounds were tested for anti-inflammatory and analgesic activities comparable to ibuprofen.

Some of the compounds showed significant activity compared to standard drug [7]. Kadi et al.(2007) synthesized novel 2- (1-adamantyl)-5-substituted-1,3,4- oxadiazoles and 2-(1 adamantylamino)- 5-substituted-1,3,4-thiadiazoles (8). The in vivo anti-inflammatory activity of the synthesized compounds was determined using the carrageenin-induced paw edema method in rats. The oxadiazole derivatives produced good dosedependent anti-inflammatory activity [8]. Jadhav et al.(2008) synthesized a series of 6-substituted and 5,6-disubstituted 2- (6-methyl-benzofuran-3-ylmethyl)- imidazo[2,1-b][1,3,4]thiadiazoles (9). The new compounds have been tested for their in vivo analgesic, antiinflammatory activities. Qualitative SAR studies indicate that the chloro substitution in the imidazole ring and introduction of formyl group at C-5 position of the imidazole ring increased the anti-inflammatory and analgesic activity [9]. Hafez et al.(2008) synthesized novel spiro-thioxanthene-9',2- [1,3,4]thiadiazoles and spiro-xanthene- 9',2-[1,3,4]thiadiazoles (10). Some of the newly synthesized compounds were tested for anti-inflammatory and analgesic activities comparable to ibuprofen. Most of the compounds showed significant activity compared to standard drug [10]. Schenone et al.(2006) synthesized two series of N-[5-oxo-4-(arylsulfonyl)-4,5- dihydro-1,3,4-thiadiazol-2-yl]-amides (11) and tested in vivo for their analgesic and anti-inflammatory activities. All the new compounds possess good antalgic action in the acetic acid writhing test and some terms of the series showed also fair antiinflammatory activity in the carrageenan rat paw edema test [11]. Amir and Kumar(2004) synthesized new 1,3,4-thiadiazoles derived from 2- [(2,6-dichloroanilino) phenyl] acetic acid (12). These compounds were tested in vivo for their anti-inflammatory activity. Some compounds showed very good anti-inflammatory activity in the carrageenin induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. The compounds, which showed less ulcerogenic action, also showed reduced malondialdehyde content (MDA), which is one of the byproduct of lipid peroxidation [12]. Gadad et al.(2008) synthesized a series of 2-trifluoromethyl/sulfonamido-5,6- diarylsubstituted imidazo[2,1-b]-1,3,4- thiadiazole derivatives (13-14). The selected compounds were evaluated for their preliminary in vitro cyclooxygenase inhibitory activity against COX-2 and COX-1 enzymes using colorimetric method. The compounds tested showed selective inhibitory activity toward COX-2 (80.6-49.4%) over COX-1 (30.6-8.6). These compounds also exhibited significant anti-inflammatory activity (70.09-42.32%), which is comparable to that of celecoxib in the carrageenaninduced rat paw edema method [13]. Palaska et al.(2002) synthesized 2-(2- naphthyloxymethyl)-5-substituted amino-1,3,4-thiadiazole derivatives (15) and evaluated as orally active antiinflammatory agents with reduced sideeffects. The anti-inflammatory and ulcerogenic activities of the compounds were compared with naproxen, indomethacin and phenylbutazone. In carrageenan-induced foot pad edema assay some compounds showed an interesting anti-inflammatory activity. Side effects of the compounds were examined on gastric mucosa, liver and stomach and none of the compounds showed significant side effects compared with reference nonsteroidal anti-inflammatory drugs (NSAIDs) [14]. Amir et al.(2007) synthesized some 6- substituted-1,2,4-triazolo[3,4-b]-1,3,4- thiadiazole derivatives (16-17) by cyclisation of 4-amino-5-[1-(6- methoxy-2-naphthyl)ethyl]-3-mercapto- (4H)-1,2,4-triazole with various substituted aromatic acids and aryl/ alkyl isothiocyanates. The compounds were evaluated for their antiinflammatory and analgesic potentials by known experimental models. Several of these showed significant activity [15]. Bhati and Kumar(2008) synthesized various N-({5-[(arylmethylene)amino]- 1,3,4-thiadiazol-2-yl}methyl) [1,3,4] thiadiazino[6,5-b]indol-3-amine (18), 2- aryl-3-{5-[([1,3,4] thiadiazino[6,5- b]indol-3-ylamino)methyl]-1,3,4- thiadiazol-2-yl}-1,3-thiazolidin-4-one (19) and 3-chloro-4-aryl-1-{5- [{[1,3,4]thiadiazino[6,5-b]indol-3- ylamino]methyl]-1,3,4-thiadiazol-2- yl}azetidin-2-one (20). One compound has shown most active antiinflammatory and analgesic activities with better ulcerogenic activity than phenylbutazone, while this compound was found to be associated with lesser degree of anti-inflammatory and analgesic activities as compared to indomethacin [16]. Bekhit et al.(2008) synthesized some thiazolyl and thiadiazolyl derivatives of 1H-pyrazole (21-22). All the target compounds showed anti-inflammatory activity and three of them surpassed that of indomethacin both locally and systemically in the cotton pellet granuloma and rat paw edema bioassay.[17]. Schenone et al.(2001) synthesized two series of 3-arylsulphonyl-5-arylamino- 1,3,4-thiadiazol-2(3H)ones (23) with potential anti-inflammatory and analgesic activity. Pharmacological results revealed that all the title compounds possess good antalgic activity and fair anti-inflammatory properties [18]. Rostom et al.(2009) described the synthesis of two groups of structure hybrids comprising basically the antipyrine moiety attached to polysubstituted 2,5-disubstituted-1,3,4-

thiadiazole (24-25) through various linkages. The newly synthesized compounds were evaluated for their anti-inflammatory activity using two different screening protocols; namely, the formalin-induced paw edema and the turpentine oil-induced granuloma pouch bioassays, using diclofenac Na as a reference standard. Meanwhile, the analgesic activity of the same compounds was evaluated using the rat tail withdrawal technique. In general, compounds belonging to the thiazolylantipyrine series exhibited better biological activities than their thiadiazolyl structure variants [19]. Kumar et al.(2008) synthesized a series of 1,3,4-thiadiazole derivatives of biphenyl-4-yloxy acetic acid (26) in order to obtain new compounds with potential anti-inflammatory activity, analgesic activity and lower ulcerogenic potential. The compounds possessing potent anti-inflammatory activity were further tested for their analgesic, ulcerogenic and antioxidant activities. Out of all tested compounds, the some compounds showed significant reduction in rat paw edema induced by carrageenan treatment [20]. Mathew et al.(2007) synthesized several 3,6-disubstituted-1,2,4- triazolo[3,4-b]-1,3,4-thiadiazole and their dihydro analogues (27). Antiinflammatory and analgesic activity screening indicated that some of the tested compounds showed good and some showed moderate antiinflammatory and analgesic activities [21]. Sharma et al.(2008) synthesized a new series of cyclooxygenase-2 inhibitors with 2-amino- -5-sulfanyl-1,3,4-thiadiazole (28) as the central scaffold unit. Some compounds exhibited significant biological activity [22]. Amir and Kumar(2007) synthesized various 1,3,4-thiadiazoles derivatives of ibuprofen (29). The cyclized derivatives were screened for their antiinflammatory activity by the carrageenan induced rat paw edema method and showed 50 to 86% inhibition, whereas the standard drug ibuprofen showed 92% inhibition at the same oral dose [23]. Mishra et al.(1992) synthesized new Nsubstituted acetyl derivetives of 2- amino-5-alkyl-1,3,4-thiadiazoles (30) and evaluated for anti-inflammatory activity. Some of the compounds showed anti-inflammatory activity [24].

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A Study by Tarek Elwakil et al. entitled "Led Light Photobiomodulation Effect on Wound Healing Combined with Phenytoin in Mice Model" is awarded Best Article of Vol 13 issue 02

A Study by Mohita Ray et al. entitled "Accuracy of Intra-Operative Frozen Section Consultation of Gastrointestinal Biopsy Samples in Correlation with the Final Histopathological Diagnosis" is awarded Best Article for Vol 13 issue 01

A Study by Badritdinova MN et al. entitled "Peculiarities of a Pain in Patients with Ischemic Heart Disease in the Presence of Individual Combines of the Metabolic Syndrome" is awarded Best Article for Vol 12 issue 24

A Study by Sindhu Priya E S et al. entitled "Neuroprotective activity of Pyrazolone Derivatives Against Paraquat-induced Oxidative Stress and Locomotor Impairment in Drosophila melanogaster" is awarded Best Article for Vol 12 issue 23

A Study by Habiba Suhail et al. entitled "Effect of Majoon Murmakki in Dysmenorrhoea (Usre Tams): A Standard Controlled Clinical Study" is awarded Best Article for Vol 12 issue 22

A Study by Ghaffar UB et al. entitled "Correlation between Height and Foot Length in Saudi Population in Majmaah, Saudi Arabia" is awarded Best Article for Vol 12 issue 21

A Study by Siti Sarah Binti Maidin entitled "Sleep Well: Mobile Application to Address Sleeping Problems" is awarded Best Article for Vol 12 issue 20

A Study by Avijit Singh"Comparison of Post Operative Clinical Outcomes Between “Made in India” TTK Chitra Mechanical Heart Valve Versus St Jude Mechanical Heart Valve in Valve Replacement Surgery" is awarded Best Article for Vol 12 issue 19

A Study by Sonali Banerjee and Mary Mathews N. entitled "Exploring Quality of Life and Perceived Experiences Among Couples Undergoing Fertility Treatment in Western India: A Mixed Methodology" is awarded Best Article for Vol 12 issue 18

A Study by Jabbar Desai et al. entitled "Prevalence of Obstructive Airway Disease in Patients with Ischemic Heart Disease and Hypertension" is awarded Best Article for Vol 12 issue 17

A Study by Juna Byun et al. entitled "Study on Difference in Coronavirus-19 Related Anxiety between Face-to-face and Non-face-to-face Classes among University Students in South Korea" is awarded Best Article for Vol 12 issue 16

A Study by Sudha Ramachandra & Vinay Chavan entitled "Enhanced-Hybrid-Age Layered Population Structure (E-Hybrid-ALPS): A Genetic Algorithm with Adaptive Crossover for Molecular Docking Studies of Drug Discovery Process" is awarded Best article for Vol 12 issue 15

A Study by Varsha M. Shindhe et al. entitled "A Study on Effect of Smokeless Tobacco on Pulmonary Function Tests in Class IV Workers of USM-KLE (Universiti Sains Malaysia-Karnataka Lingayat Education Society) International Medical Programme, Belagavi" is awarded Best article of Vol 12 issue 14, July 2020

A study by Amruta Choudhary et al. entitled "Family Planning Knowledge, Attitude and Practice Among Women of Reproductive Age from Rural Area of Central India" is awarded Best Article for special issue "Modern Therapeutics Applications"

A study by Raunak Das entitled "Study of Cardiovascular Dysfunctions in Interstitial Lung Diseas epatients by Correlating the Levels of Serum NT PRO BNP and Microalbuminuria (Biomarkers of Cardiovascular Dysfunction) with Echocardiographic, Bronchoscopic and HighResolution Computed Tomography Findings of These ILD Patients" is awarded Best Article of Vol 12 issue 13

A Study by Kannamani Ramasamy et al. entitled "COVID-19 Situation at Chennai City – Forecasting for the Better Pandemic Management" is awarded best article for Vol 12 issue 12

A Study by Muhammet Lutfi SELCUK and Fatma entitled "Distinction of Gray and White Matter for Some Histological Staining Methods in New Zealand Rabbit's Brain" is awarded best article for Vol 12 issue 11

A Study by Anamul Haq et al. entitled "Etiology of Abnormal Uterine Bleeding in Adolescents – Emphasis Upon Polycystic Ovarian Syndrome" is awarded best article for Vol 12 issue 10

A Study by entitled "Estimation of Reference Interval of Serum Progesterone During Three Trimesters of Normal Pregnancy in a Tertiary Care Hospital of Kolkata" is awarded best article for Vol 12 issue 09

A Study by Ilona Gracie De Souza & Pavan Kumar G. entitled "Effect of Releasing Myofascial Chain in Patients with Patellofemoral Pain Syndrome - A Randomized Clinical Trial" is awarded best article for Vol 12 issue 08

A Study by Virendra Atam et. al. entitled "Clinical Profile and Short - Term Mortality Predictors in Acute Stroke with Emphasis on Stress Hyperglycemia and THRIVE Score : An Observational Study" is awarded best article for Vol 12 issue 07

A Study by K. Krupashree et. al. entitled "Protective Effects of Picrorhizakurroa Against Fumonisin B1 Induced Hepatotoxicity in Mice" is awarded best article for issue Vol 10 issue 20

A study by Mithun K.P. et al "Larvicidal Activity of Crude Solanum Nigrum Leaf and Berries Extract Against Dengue Vector-Aedesaegypti" is awarded Best Article for Vol 10 issue 14 of IJCRR

A study by Asha Menon "Women in Child Care and Early Education: Truly Nontraditional Work" is awarded Best Article for Vol 10 issue 13

A study by Deep J. M. "Prevalence of Molar-Incisor Hypomineralization in 7-13 Years Old Children of Biratnagar, Nepal: A Cross Sectional Study" is awarded Best Article for Vol 10 issue 11 of IJCRR

A review by Chitra et al to analyse relation between Obesity and Type 2 diabetes is awarded 'Best Article' for Vol 10 issue 10 by IJCRR.

A study by Karanpreet et al "Pregnancy Induced Hypertension: A Study on Its Multisystem Involvement" is given Best Paper Award for Vol 10 issue 09

List of Awardees

A Study by Ese Anibor et al. "Evaluation of Temporomandibular Joint Disorders Among Delta State University Students in Abraka, Nigeria" from Vol 13 issue 16 received Emerging Researcher Award

A Study by Alkhansa Mahmoud et al. entitled "mRNA Expression of Somatostatin Receptors (1-5) in MCF7 and MDA-MB231 Breast Cancer Cells" from Vol 13 issue 06 received Emerging Researcher Award

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