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In silico molecular docking and in vitro antidiabetic studies of dihydropyrimido[4,5-a]acridin-2-amines.

Bharathi A, Roopan SM, Vasavi CS, Munusami P, Gayathri GA, Gayathri M - Biomed Res Int (2014)

Bottom Line: An in vitro antidiabetic activity on α -amylase and α -glucosidase activity of novel 10-chloro-4-(2-chlorophenyl)-12-phenyl-5,6-dihydropyrimido[4,5-a]acridin-2-amines (3a-3f) were evaluated.An in silico molecular docking was performed on synthesized molecules (3a-3f).Overall studies indicate that compound 3e is a promising compound leading to the development of selective inhibition of α -amylase and α -glucosidase.

View Article: PubMed Central - PubMed

Affiliation: Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore, Tamil Nadu 632 014, India.

ABSTRACT
An in vitro antidiabetic activity on α -amylase and α -glucosidase activity of novel 10-chloro-4-(2-chlorophenyl)-12-phenyl-5,6-dihydropyrimido[4,5-a]acridin-2-amines (3a-3f) were evaluated. Structures of the synthesized molecules were studied by FT-IR, (1)H NMR, (13)C NMR, EI-MS, and single crystal X-ray structural analysis data. An in silico molecular docking was performed on synthesized molecules (3a-3f). Overall studies indicate that compound 3e is a promising compound leading to the development of selective inhibition of α -amylase and α -glucosidase.

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The packing of the molecules in the unit cell, viewed down the a-axis with the hydrogen bond geometry of compound 3f.
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fig3: The packing of the molecules in the unit cell, viewed down the a-axis with the hydrogen bond geometry of compound 3f.

Mentions: Crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the 10-chloro-4-(2-chlorophenyl)-12-phenyl-5,6-dihydropyrimido[4,5-a]acridin-2-amine, 3f, in ethyl acetate. The measurements were made on Enraf Nonius CAD4-MV31 single crystal X-ray diffractometer. The diagrams and calculations have been performed using SAINT (APEX II) for frame integration, SHELXTL for structure solution and refinement software programs. The structure was refined using the full-matrix least squares procedures on F2 with anisotropic thermal parameters for all nonhydrogen atoms. The crystal data and details concerning data collection and structure refinement of compound, 3f, single crystal are summarized in Table 2. As we can see compound 3f crystallizes in triclinic space group, P-1. The single crystal structure and atomic numbering chosen for compound 3f are demonstrated in Figure 2. Selected bond lengths and bond angles are compiled in Table 3. It can be observed that the bond lengths of all kind atoms on the whole molecule are absorbed. The typical C–C single (1.55 Å) and C=C double (1.38 Å) bonds, C–N typical single (1.35 Å) and C=N double (1.33 Å) bonds. This means that the carbon-carbon bond and the carbon-nitrogen bond have double bond character and contribute to form conjugated system. Furthermore, carbon attached with strong electronegative atom chlorine bond length is C–Cl (1.68 A), in case all C–H (0.97 A) and C=H (0.93 A) are absorbed. The primary amine hydrogen bond length is N–H (0.86 A), respectively (Table 3). Concerning inspection of the torsion angles, the 3f molecule has nearly planar core. Figure 3 illustrates a representative view of compound 3f crystal packing structure. The two molecules of compound 3f are packed in face-to-face arrangement due to the intermolecular hydrogen bonds. The crystal packing structure demonstrates the existence of two intermolecular hydrogen bonds. Interesting result were absorbed from crystal packing structure is the intermolecular hydrogen bonding occurs at C(23)–H(23) and C(24)–H(24) of one molecule to another neighbouring molecule of C(23)–H(23) and C(24)–H(24), not in the case of primary amine containing two hydrogen N(4)–H(A) and N(4)–H(B) Figure 3.


In silico molecular docking and in vitro antidiabetic studies of dihydropyrimido[4,5-a]acridin-2-amines.

Bharathi A, Roopan SM, Vasavi CS, Munusami P, Gayathri GA, Gayathri M - Biomed Res Int (2014)

The packing of the molecules in the unit cell, viewed down the a-axis with the hydrogen bond geometry of compound 3f.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4060768&req=5

fig3: The packing of the molecules in the unit cell, viewed down the a-axis with the hydrogen bond geometry of compound 3f.
Mentions: Crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the 10-chloro-4-(2-chlorophenyl)-12-phenyl-5,6-dihydropyrimido[4,5-a]acridin-2-amine, 3f, in ethyl acetate. The measurements were made on Enraf Nonius CAD4-MV31 single crystal X-ray diffractometer. The diagrams and calculations have been performed using SAINT (APEX II) for frame integration, SHELXTL for structure solution and refinement software programs. The structure was refined using the full-matrix least squares procedures on F2 with anisotropic thermal parameters for all nonhydrogen atoms. The crystal data and details concerning data collection and structure refinement of compound, 3f, single crystal are summarized in Table 2. As we can see compound 3f crystallizes in triclinic space group, P-1. The single crystal structure and atomic numbering chosen for compound 3f are demonstrated in Figure 2. Selected bond lengths and bond angles are compiled in Table 3. It can be observed that the bond lengths of all kind atoms on the whole molecule are absorbed. The typical C–C single (1.55 Å) and C=C double (1.38 Å) bonds, C–N typical single (1.35 Å) and C=N double (1.33 Å) bonds. This means that the carbon-carbon bond and the carbon-nitrogen bond have double bond character and contribute to form conjugated system. Furthermore, carbon attached with strong electronegative atom chlorine bond length is C–Cl (1.68 A), in case all C–H (0.97 A) and C=H (0.93 A) are absorbed. The primary amine hydrogen bond length is N–H (0.86 A), respectively (Table 3). Concerning inspection of the torsion angles, the 3f molecule has nearly planar core. Figure 3 illustrates a representative view of compound 3f crystal packing structure. The two molecules of compound 3f are packed in face-to-face arrangement due to the intermolecular hydrogen bonds. The crystal packing structure demonstrates the existence of two intermolecular hydrogen bonds. Interesting result were absorbed from crystal packing structure is the intermolecular hydrogen bonding occurs at C(23)–H(23) and C(24)–H(24) of one molecule to another neighbouring molecule of C(23)–H(23) and C(24)–H(24), not in the case of primary amine containing two hydrogen N(4)–H(A) and N(4)–H(B) Figure 3.

Bottom Line: An in vitro antidiabetic activity on α -amylase and α -glucosidase activity of novel 10-chloro-4-(2-chlorophenyl)-12-phenyl-5,6-dihydropyrimido[4,5-a]acridin-2-amines (3a-3f) were evaluated.An in silico molecular docking was performed on synthesized molecules (3a-3f).Overall studies indicate that compound 3e is a promising compound leading to the development of selective inhibition of α -amylase and α -glucosidase.

View Article: PubMed Central - PubMed

Affiliation: Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore, Tamil Nadu 632 014, India.

ABSTRACT
An in vitro antidiabetic activity on α -amylase and α -glucosidase activity of novel 10-chloro-4-(2-chlorophenyl)-12-phenyl-5,6-dihydropyrimido[4,5-a]acridin-2-amines (3a-3f) were evaluated. Structures of the synthesized molecules were studied by FT-IR, (1)H NMR, (13)C NMR, EI-MS, and single crystal X-ray structural analysis data. An in silico molecular docking was performed on synthesized molecules (3a-3f). Overall studies indicate that compound 3e is a promising compound leading to the development of selective inhibition of α -amylase and α -glucosidase.

Show MeSH
Related in: MedlinePlus