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Three-component synthesis of pyrano[2,3-d]-pyrimidine dione derivatives facilitated by sulfonic acid nanoporous silica (SBA-Pr-SO3H) and their docking and urease inhibitory activity.

Ziarani GM, Faramarzi S, Asadi S, Badiei A, Bazl R, Amanlou M - Daru (2013)

Bottom Line: The compounds with electron donating group and higher hydrophobic interaction with active site of enzyme prevents hydrolysis of substrate.Electron withdrawing groups such as nitro at different position and meta-methoxy reduced urease inhibitory activity.Substitution of both hydrogen of barbituric acid with methyl group will convert inhibitor to activator.

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Affiliation: Department of Chemistry, Alzahra University, Vanak Square, P,O, Box 19938939973, Tehran, Iran. gmziarani@hotmail.com.

ABSTRACT

Background: A straightforward and efficient method for the synthesis of pyrano[2,3-d]pyrimidine diones derivatives from the reaction of barbituric acid, malononitrile and various aromatic aldehydes using SBA-Pr-SO3H as a nanocatalyst is reported.

Results: Reactions proceed with high efficiency under solvent free conditions. Urease inhibitory activity of pyrano[2,3-d]pyrimidine diones derivatives were tested against Jack bean urease using phenol red method. Three compounds of 4a, 4d and 4l were not active in urease inhibition test, but compound 4a displayed slight urease activation properties. Compounds 4b, 4k, 4f, 4e, 4j, 4g and 4c with hydrophobic substitutes on phenyl ring, showed good inhibitory activity (19.45-279.14 μM).

Discussion: The compounds with electron donating group and higher hydrophobic interaction with active site of enzyme prevents hydrolysis of substrate. Electron withdrawing groups such as nitro at different position and meta-methoxy reduced urease inhibitory activity. Substitution of both hydrogen of barbituric acid with methyl group will convert inhibitor to activator.

No MeSH data available.


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SBA-Pr-SO3H act as a nano-reactor in this reaction.
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Figure 2: SBA-Pr-SO3H act as a nano-reactor in this reaction.

Mentions: In conclusion we have developed a nano-catalyzed multicomponent synthesis of pyrano pyrimidine diones in good to very good yields. In comparison with previous investigations (Table 3), we presented SBA-Pr-SO3H as an efficient and active nano-reactor (Figure 2). Our method is simple as no special apparatus, reagents or chemicals, and work up are required, and the formed compound is filtered and purified just by simple crystallization. This synthesis is also advantageous in terms of atom economy as well as is devoid of any hazardous chemicals. The urease inhibitory activity of pyrano[2,3-d]pyrimidine dione derivatives were reported for first time.


Three-component synthesis of pyrano[2,3-d]-pyrimidine dione derivatives facilitated by sulfonic acid nanoporous silica (SBA-Pr-SO3H) and their docking and urease inhibitory activity.

Ziarani GM, Faramarzi S, Asadi S, Badiei A, Bazl R, Amanlou M - Daru (2013)

SBA-Pr-SO3H act as a nano-reactor in this reaction.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3584946&req=5

Figure 2: SBA-Pr-SO3H act as a nano-reactor in this reaction.
Mentions: In conclusion we have developed a nano-catalyzed multicomponent synthesis of pyrano pyrimidine diones in good to very good yields. In comparison with previous investigations (Table 3), we presented SBA-Pr-SO3H as an efficient and active nano-reactor (Figure 2). Our method is simple as no special apparatus, reagents or chemicals, and work up are required, and the formed compound is filtered and purified just by simple crystallization. This synthesis is also advantageous in terms of atom economy as well as is devoid of any hazardous chemicals. The urease inhibitory activity of pyrano[2,3-d]pyrimidine dione derivatives were reported for first time.

Bottom Line: The compounds with electron donating group and higher hydrophobic interaction with active site of enzyme prevents hydrolysis of substrate.Electron withdrawing groups such as nitro at different position and meta-methoxy reduced urease inhibitory activity.Substitution of both hydrogen of barbituric acid with methyl group will convert inhibitor to activator.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Alzahra University, Vanak Square, P,O, Box 19938939973, Tehran, Iran. gmziarani@hotmail.com.

ABSTRACT

Background: A straightforward and efficient method for the synthesis of pyrano[2,3-d]pyrimidine diones derivatives from the reaction of barbituric acid, malononitrile and various aromatic aldehydes using SBA-Pr-SO3H as a nanocatalyst is reported.

Results: Reactions proceed with high efficiency under solvent free conditions. Urease inhibitory activity of pyrano[2,3-d]pyrimidine diones derivatives were tested against Jack bean urease using phenol red method. Three compounds of 4a, 4d and 4l were not active in urease inhibition test, but compound 4a displayed slight urease activation properties. Compounds 4b, 4k, 4f, 4e, 4j, 4g and 4c with hydrophobic substitutes on phenyl ring, showed good inhibitory activity (19.45-279.14 μM).

Discussion: The compounds with electron donating group and higher hydrophobic interaction with active site of enzyme prevents hydrolysis of substrate. Electron withdrawing groups such as nitro at different position and meta-methoxy reduced urease inhibitory activity. Substitution of both hydrogen of barbituric acid with methyl group will convert inhibitor to activator.

No MeSH data available.


Related in: MedlinePlus