Application of UV-Vis spectrophotometric process for the assessment of indoloacridines as free radical scavenger.

A conventional approach has been used to synthesis Indole fused acridine, 4a-e. In this paper to achieve the target molecule, 4 the reaction was performed via two steps. In step 1, there was a reaction between Carbazolone, 1 and benzophenone, 2 to get dihydroindoloacridine, 3. In step 2, compound, 3 was treated with 5% Palladium/Carbon in the presence of diphenyl ether for 5h to give a dark brown product, 4. The column chromatography was used to purify final product, 4. All the synthesized compounds such as 3 and 4 were characterized by melting point, FTIR, (1)H NMR, and Mass spectra. Further to check the purity of the compounds it was subjected to CHN analyzer. The target molecules such as 3 and 4 were screened for antimicrobial studies against bacteria such as Bacillus subtilis (B. subtilis), Staphylococcus aureus (S. aureus), Klebsiella pneumonia (K. pneumonia), Salmonella typhi (S. typhi); and fungi like Aspergillus niger (A. niger), Aspergillus fumigatus (A. fumigatus). The obtained results clearly proves that the target molecules shown reasonable activity against K. pneumonia and A. niger. Further the compounds were screened for free radical scavenging activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH). The free radical scavenging property was performed using UV-Visible spectroscopy. The results were compared with the standard BHT (Butylated Hydroxy Toluene). Compounds, 4a and 4e were shown higher percentage of inhibition when compare to the standard. The result confirms that further research on indoloacridine will leads effective drug to the market.

7-(4-Meth-oxy-phen-yl)-4,9-dimethyl-N-(4-methyl-phen-yl)-5,12-diaza-tetra-phen-6-amine.

In the title compound, C(32)H(27)N(3)O, the fused tetra-cycilc ring system is essentially planar [r.m.s. deviation = 0.07 (7) Å]. An intra-molecular N-H⋯π(arene) inter-action and a weak intra-molecular C-H⋯N hydrogen bond may influence the mol-ecular conformation. In the crystal, weak inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into centrosymmetric dimers, forming R(2) (2)(14) motifs. In addition, weak π-π stacking inter-actions with centroid-centroid distances in the range 3.578 (1)-3.739 (1) Šprovide further stabilization.

4-Chloro-6-methyl-N-(4-methyl-phen-yl)quinolin-2-amine.

In the title compound C(17)H(15)ClN(2), the dihedral angle between the quinoline ring system and the phenyl ring is 50.18 (6)°. In the crystal, mol-ecules are linked into chains running along the c axis by N-H⋯N hydrogen bonds.

2-Chloro-7-methyl-12-phenyldibenzo[b,g][1,8]naphthyridin-11(6H)-one.

In the title compound, C(23)H(15)ClN(2)O, the fused ring system is planar: the deviation of all the non-H atoms from the plane through all four fused rings is less than 0.31 Å. The plane of the phenyl ring is inclined at 71.78 (5)° to the mean plane of the 1,8-naphthrydine ring system. The crystal structure is devoid of any classical hydrogen bonds but π-π inter-actions are present.

4-Chloro-2,5-dimethyl-quinoline.

Mol-ecules of the title compound, C(11)H(10)ClN, are essentially planar (r.m.s. deviation for all non-H atoms = 0.009 Å) and are stacked along the a axis with the centroids of the benzene and pyridine rings alternately separated by 3.649 (1) and 3.778 (1) Å.

2,9-Dimethyl-7-phenyl-N-(4-methyl-phen-yl)dibenzo[b,h][1,6]naphthyridin-6-amine.

The title compound, C(31)H(25)N(3), was synthesized from 6,4',4''-trimethyl-2,4-bis-(N-phenyl-amino)-quinoline and is the first structural example containing a phenyl and phenyl-amino fragment attached to a fused dibenzo[1,6]naphthyridine moiety. The fused tetra-cyclic ring system is essentially planar [r.m.s. deviation = 0.08 (3) Å]. The phenyl ring and the phenyl-amino group are inclined by 82.68 (6) and 35.31 (5)°, respectively, to the mean plane of the fused tetra-cyclic ring system. A weak intra-molecular N-H⋯π(arene) inter-action may in part influence the conformation of the mol-ecule. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯N hydrogen bonds into centrosymmetric dimers. Additional stabilization is provided by weak C-H⋯π and π-π stacking inter-actions [centroid-centroid distances = 3.834 (2) and 3.898 (1) Å].

7-(2-Chloro-phen-yl)-2,6,9-trimethyl-dibenzo[b,h][1,6]naphthyridine.

In the title compound, C(25)H(19)ClN(2), the dibenzo[b,h][1,6]naphthyridine system is planar to within 0.16 (2) Å, and the chloro-phenyl ring is inclined to it by 82.53 (7)°. In the crystal, mol-ecules are linked by C-H⋯N hydrogen bonds, forming chains propagating in [100]. There are also a number of weak π-π stacking inter-actions present [centroid-centroid distances = 3.8531 (1) and 3.7631 (1) Å].

7,8,9,10-Tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

In the title mol-ecule, C(13)H(13)NO, the dihedral angle between the benzene and pyrrole rings is 1.05 (5)°. The cyclo-heptene ring adopts a slightly distorted boat conformation. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds form centrosymmetric dimers. A C-H⋯π inter-action, involving the benzene ring, is also found in the structure.

6-Meth-oxy-2,3,4,9-tetra-hydro-1H-carbazol-1-one.

The carbazole unit of the title mol-ecule, C(13)H(13)NO(2), is not planar. The dihedral angle between the benzene ring and the pyrrole ring is 1.69 (6)°. The cyclo-hexene ring adopts an envelope conformation. Inter-molecular C-H⋯O and N-H⋯O hydrogen bonds are present in the crystal structure. A C-H⋯π inter-action, involving the benzene ring, is also found in the crystal structure.

6-Chloro-3,4-di-hydro-9H-carbazol-1(2H)-one.

The carbazole unit of the title mol-ecule, C(12)H(10)ClNO, is not planar. The dihedral angle between the benzene and pyrrole rings is 1.35 (10)°. The cyclo-hexene ring adopts an envelope conformation. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds form centrosymmetric dimers.