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Synthesis and antiulcer activity evaluation of conjugates of amino acids with N-aroyl- N, N'-dicyclohexyl urea.

Subudhi BB, Sahoo SP - Chem Cent J (2011)

Bottom Line: Amino acids are safe molecules with variable efficacy against ulceration.All these compounds were found to be safe and active.The promising efficacy and safety of these compounds is interesting for further investigation.

View Article: PubMed Central - HTML - PubMed

Affiliation: School of Pharmaceutical Sciences, Siksha O Anusandhan University Bhubaneswar, Orissa, 751003, India. bharatbhusans@gmail.com.

ABSTRACT
Amino acids are safe molecules with variable efficacy against ulceration. Considering the good antioxidant potential of N-aroyl- N, N'-dicyclohexyl urea and antiulcer activities of amino acids, a series of amino acid conjugates of N-aroyl- N, N'-dicyclohexyl urea was synthesized and the effect against ulceration in albino rats induced by pyloric ligation was screened. All these compounds were found to be safe and active. Reduction of ulcer index was significant for all compounds. Conjugates of methionine and histidine exhibited enhanced antiulcer activity comparable to omeprazole in terms of inhibition of release of gastric juice, hydrochloric acid and neutralization activity. The promising efficacy and safety of these compounds is interesting for further investigation.

No MeSH data available.


Related in: MedlinePlus

Reduction in free acidity and total acidity by the compounds (3a-j).
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Figure 2: Reduction in free acidity and total acidity by the compounds (3a-j).

Mentions: The newly synthesized compounds exhibited variable antiulcer and antisecretory activity (Table 2). Reduction in volume of gastric juice was significant (P < 0.001) compared to control for 3a, 3b, 3c, 3d, 3g, 3h, 3i and 3j indicating their good antisecretory potential. The extent of reduction of secretion of gastric juice for compound 3b, 3c and 3j (Figure 1) was similar to that of omeprazole. The acid neutralizing capacity as indicated by pH of the gastric fluid was found to be more for compound 3j. All other compounds except 3e, 3f and 3h exhibited significant (P < 0.001) acid neutralizing capacity. Compound 3b and 3c showed antisecretory activity comparable to omeprazole but their acid neutralizing activity was found to be lower than the standard. Significant (P < 0.001) reduction in free acidity in all compounds except compound 3a indicated the ability of test compounds to inhibit secretion of hydrochloric acid. This inhibition was higher for the compound 3j and 3c followed by that of 3b. Reduction in free acidity of compound 3j and 3c was comparable to that of standard. All the compounds that inhibited free acidity, a proportionate inhibitory activity on total acidity was also observed (Figure 2). From the reduction in total acidity value, capacity of these compounds to reduce secretion as well as neutralize acid can be suggested. The inhibition of total acidity was highest for compounds 3c and 3j. The potential of the test compounds for inhibiting hydrochloric acid, gastric juice and neutralizing acidity has resulted in protection of gastric mucosa as observed from the significant (P < 0.001) decrease in ulcer index. From the analysis of the data it was observed that compound 3c containing methionine as the substituent and 3j with histidine as the substituent exhibited enhanced antiulcer activity that is comparable to omeprazole in terms of inhibition of release of gastric juice, hydrochloric acid and neutralization activity. Conjugates of tyrosine, serine, glutamine and cysteine exhibited similar anti-secretory and acid neutralizing capacity. Their antiulcer activity was significant compared to control but were less effective compared to conjugates of methionine and histidine. Conjugates of valine and threonine were least effective in reducing gastric volume. However the reduction of ulcer index was significant. This can be attributed to their effect on reduction of hydrochloric acid as observed from their free acidity and total acidity values. This study has yielded some very safe new compounds with good antiulcer potential.


Synthesis and antiulcer activity evaluation of conjugates of amino acids with N-aroyl- N, N'-dicyclohexyl urea.

Subudhi BB, Sahoo SP - Chem Cent J (2011)

Reduction in free acidity and total acidity by the compounds (3a-j).
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3275514&req=5

Figure 2: Reduction in free acidity and total acidity by the compounds (3a-j).
Mentions: The newly synthesized compounds exhibited variable antiulcer and antisecretory activity (Table 2). Reduction in volume of gastric juice was significant (P < 0.001) compared to control for 3a, 3b, 3c, 3d, 3g, 3h, 3i and 3j indicating their good antisecretory potential. The extent of reduction of secretion of gastric juice for compound 3b, 3c and 3j (Figure 1) was similar to that of omeprazole. The acid neutralizing capacity as indicated by pH of the gastric fluid was found to be more for compound 3j. All other compounds except 3e, 3f and 3h exhibited significant (P < 0.001) acid neutralizing capacity. Compound 3b and 3c showed antisecretory activity comparable to omeprazole but their acid neutralizing activity was found to be lower than the standard. Significant (P < 0.001) reduction in free acidity in all compounds except compound 3a indicated the ability of test compounds to inhibit secretion of hydrochloric acid. This inhibition was higher for the compound 3j and 3c followed by that of 3b. Reduction in free acidity of compound 3j and 3c was comparable to that of standard. All the compounds that inhibited free acidity, a proportionate inhibitory activity on total acidity was also observed (Figure 2). From the reduction in total acidity value, capacity of these compounds to reduce secretion as well as neutralize acid can be suggested. The inhibition of total acidity was highest for compounds 3c and 3j. The potential of the test compounds for inhibiting hydrochloric acid, gastric juice and neutralizing acidity has resulted in protection of gastric mucosa as observed from the significant (P < 0.001) decrease in ulcer index. From the analysis of the data it was observed that compound 3c containing methionine as the substituent and 3j with histidine as the substituent exhibited enhanced antiulcer activity that is comparable to omeprazole in terms of inhibition of release of gastric juice, hydrochloric acid and neutralization activity. Conjugates of tyrosine, serine, glutamine and cysteine exhibited similar anti-secretory and acid neutralizing capacity. Their antiulcer activity was significant compared to control but were less effective compared to conjugates of methionine and histidine. Conjugates of valine and threonine were least effective in reducing gastric volume. However the reduction of ulcer index was significant. This can be attributed to their effect on reduction of hydrochloric acid as observed from their free acidity and total acidity values. This study has yielded some very safe new compounds with good antiulcer potential.

Bottom Line: Amino acids are safe molecules with variable efficacy against ulceration.All these compounds were found to be safe and active.The promising efficacy and safety of these compounds is interesting for further investigation.

View Article: PubMed Central - HTML - PubMed

Affiliation: School of Pharmaceutical Sciences, Siksha O Anusandhan University Bhubaneswar, Orissa, 751003, India. bharatbhusans@gmail.com.

ABSTRACT
Amino acids are safe molecules with variable efficacy against ulceration. Considering the good antioxidant potential of N-aroyl- N, N'-dicyclohexyl urea and antiulcer activities of amino acids, a series of amino acid conjugates of N-aroyl- N, N'-dicyclohexyl urea was synthesized and the effect against ulceration in albino rats induced by pyloric ligation was screened. All these compounds were found to be safe and active. Reduction of ulcer index was significant for all compounds. Conjugates of methionine and histidine exhibited enhanced antiulcer activity comparable to omeprazole in terms of inhibition of release of gastric juice, hydrochloric acid and neutralization activity. The promising efficacy and safety of these compounds is interesting for further investigation.

No MeSH data available.


Related in: MedlinePlus