Article

Novel N-phenylcarbamothioylbenzamides with anti-inflammatory activity and prostaglandin E2 inhibitory properties

Nov 27, 2013

DOI: doi: [10.2147/DDDT.S46691]

Published in: Drug Des Devel Ther. 2013; 7: 883–892.

Publisher: Dovepress

Carmen Limban 1 Alexandru Vasile Missir 1 Khairi Mustafa Salem Fahelelbom 2 Moawia Mohammad Al-Tabakha 2 Miron Teodor Caproiu

A number of 2-((4-ethylphenoxy)methyl)-N-(substituted-phenylcarbamothioyl) benzamides (1a–h) were synthesized via reaction of 2-((4-ethylphenoxy)methyl)benzoyl isothiocyanate (2) as a key intermediate with several substituted primary aromatic amines. The new compounds were characterized by proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), infrared spectrometry (IR), mass spectrometry (MS), and elemental analysis. The anti-inflammatory activity of 1a–h was investigated by acute carrageenan-induced paw edema in mice using the reference drug indomethacin. The results obtained indicated that, of the derivatives developed, 1a and 1d–h exhibited significantly higher anti-inflammatory activity (26.81%–61.45%) when compared with the reference drug indomethacin (22.43%) (P = 0.0490 for 1a, 0.0015 for 1d, 0.0330 for 1f, and P < 0.001 for 1e and 1h). Moreover, the ulcer incidence of 20% for 1e and 1h was clearly lower when compared with the indomethacin group (in which the ulcer incidence was 80%). Of particular note, the ulcer index of 0.2 for 1e was significantly less than that in the indomethacin group (0.6, P = 0.014). Additionally, prostaglandin E2 (PGE2) inhibitory properties were found to be high with 1e (68.32 pg/mL), significantly different from those of the placebo group (530.13 pg/mL, P < 0.001), and equipotent to the effect observed in the indomethacin-pretreated group (96.13 pg/mL, P > 0.05). Moreover, the PGE2 level of 54.15 pg/mL with 1h was also significantly different from that of the placebo group (P < 0.001) and of the indomethacin group (P < 0.05). The significant inhibition of PGE2 observed with 1e (68.32 pg/mL) and 1h (54.15 pg/mL) agree with their observed ulcer incidences. Our overall findings for N-phenylcarbamothioylbenzamides 1a–h clearly suggest that the compounds exhibit an anti-inflammatory effect, potently inhibit PGE2 synthesis, and markedly demonstrate low ulcer incidence.

Other Researches

Quality Attributes and In Vitro Bioequivalence of Different Brands of Amoxicillin Trihydrate Tablets

Abstract: Bacterial resistance and antibiotic drug effectiveness can be related to administering generic products with a subtherapeutic dose or poor in vivo drug release. The aim of this study was to investigate whether locally marketed amoxicilli...

The Impact of Modern Pharmacy Curriculum on the Student Attitude towards Weight Loss Product Advertisements: A Case Study.

Abstract: Objective: To investigate whether particular courses in modern pharmacy curriculum equips enrolled students with knowledge/skills to differentiate between different claims of weight loss products. Methods: Claims from weight loss products...

Evaluation of Certain Pharmaceutical Quality Attributes of Lisinopril Split Tablets

Abstract: Tablet splitting is an accepted practice for the administration of drugs for a variety of reasons, including dose adjustment, ease of swallowing and cost savings. The purpose of this study was to evaluate the physical properties of lisin...

Performances of New Generation of Delayed Release Capsules

Abstract: Objective: The purpose of this study was to verify the claimed acid-resistant properties and other performance indicators for AR Caps (Capsule 5 from CapsCanada) and DRcaps (Capsule 6 from Capsugel) and compare them with the immediate re...

Influence of capsule shell composition on the performance indicators of hypromellose capsule in comparison to hard gelatin capsules

The purpose of this study was to assess the in vitro performances of “vegetable” capsules in comparison to hard gelatin capsules in terms of shell weight variation, reaction to different humidity conditions, resistance to stress in the absence of mo...

DRUG INFORMATION IN COMMUNITY PHARMACY AND OUTPATIENT PHARMACY IN AL AIN CITY, U.A.E.: A DESCRIPTIVE STUDY

ABSTRACT The purpose of this study was to find out if the pharmacists working in community pharmacy and outpatient pharmacy have undergone any formal education regarding drug information, and to describe the drug information resources available,...

Antimicrobial Prospect of Newly Synthesized 1,3-Thiazole Derivatives

Abstract: A new series of 1,3-thiazole and benzo[d]thiazole derivatives 10–15 has been developed, characterized, and evaluated for in vitro antimicrobial activity at concentrations of 25–200 μg/mL against Gram+ve organisms such as methicillin-resi...

Synthesis and Calcium Channel Blocking Activity of 1, 4-Dihydropyridine Derivatives Containing Ester Substitute and Phenyl Carbamoyl Group

Abstract: Problem statement: Several studies on the synthesis of new nifedipine analogs have been carried out, but the literature reveled that no study on the synthesis and calcium channel blocking activity of the substituted ester with an amide (5-...

Synthesis, Characterization, and Antimicrobial Evaluation of Oxadiazole Congeners

A series of 1,3-oxazole, 1,3-thiazole, isomeric 1,2,4-oxadiazole, 1,3,4-oxadiazole, and 1,2,3,4-tetrazole heterocycles was synthesized. All the compounds shared as a common feature the presence of a 4-hydroxyphenyl substituent. The structures of the...