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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.

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

(a) SEM and (b) TEM images of SBA-Pr-SO3H.
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Figure 1: (a) SEM and (b) TEM images of SBA-Pr-SO3H.

Mentions: Pure Nanoporous compound SBA-15 was synthesized according to the well-established method designed by Zhao & coworkers [42] with triblock poly(ethylene oxide)-b-poly(propylene oxide)-b-poly(ethylene oxide) copolymer (Pluronic, EO20PO70EO20, P123) as the template. The SBA-15 silica was functionalized with (3-mercaptopropyl)trimethoxysilane (MPTS) and then, the thiol groups were oxidized to sulfonic acid by hydrogen peroxide. Analyzing of the catalyst surface was performed by various methods such as TGA, BET and CHN methods which demonstrated that the propylsulfonic acids were immobilized into the pores. Calculating average pore diameter of the surface area was performed by the BET method and pore volume of SBA-Pr-SO3H are 440 m2 g-1, 6.0 nm and 0.660 cm3 g-1, respectively, which are smaller than those of SBA-15 due to the immobilization of sulfonosilane groups into the pores [40]. The TGA analysis of SBA-Pr-SO3H confirmed the amount of organic groups on SBA-15. The weight reduction of SBA-Pr-SO3H in the temperature range between 200-600°C indicated that the amount of organic group was 1.2 mmol/g. SEM image of SBA-Pr-SO3H (Figure 1a) shows uniform particles about 1μm. The same morphology was observed for SBA-15. It can be concluded that morphology of acid catalyst was saved without change during the surface modifications. On the other hand, the TEM image (Figure 1b) reveals the parallel channels, which resemble to the pores configuration of SBA-15. This indicates that the pore of SBA-Pr-SO3H was not collapsed during two steps reactions.


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)

(a) SEM and (b) TEM images of SBA-Pr-SO3H.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

Figure 1: (a) SEM and (b) TEM images of SBA-Pr-SO3H.
Mentions: Pure Nanoporous compound SBA-15 was synthesized according to the well-established method designed by Zhao & coworkers [42] with triblock poly(ethylene oxide)-b-poly(propylene oxide)-b-poly(ethylene oxide) copolymer (Pluronic, EO20PO70EO20, P123) as the template. The SBA-15 silica was functionalized with (3-mercaptopropyl)trimethoxysilane (MPTS) and then, the thiol groups were oxidized to sulfonic acid by hydrogen peroxide. Analyzing of the catalyst surface was performed by various methods such as TGA, BET and CHN methods which demonstrated that the propylsulfonic acids were immobilized into the pores. Calculating average pore diameter of the surface area was performed by the BET method and pore volume of SBA-Pr-SO3H are 440 m2 g-1, 6.0 nm and 0.660 cm3 g-1, respectively, which are smaller than those of SBA-15 due to the immobilization of sulfonosilane groups into the pores [40]. The TGA analysis of SBA-Pr-SO3H confirmed the amount of organic groups on SBA-15. The weight reduction of SBA-Pr-SO3H in the temperature range between 200-600°C indicated that the amount of organic group was 1.2 mmol/g. SEM image of SBA-Pr-SO3H (Figure 1a) shows uniform particles about 1μm. The same morphology was observed for SBA-15. It can be concluded that morphology of acid catalyst was saved without change during the surface modifications. On the other hand, the TEM image (Figure 1b) reveals the parallel channels, which resemble to the pores configuration of SBA-15. This indicates that the pore of SBA-Pr-SO3H was not collapsed during two steps reactions.

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