Sharif Digital Repository

In recent years, there has been increasing interest in damaged DNA and RNA nucleobases. These damaged nucleobases can cause DNA mutation, resulting in various diseases such as cancer. Alkylating agents are mutagenic and carcinogenic in a variety of prokaryotic and eukaryotic organisms. The present study employs density functional theory (DFT/B3LYP) with the 6-311++G(d,p) basis set to investigate the effect of chemical damage in O-alkyl pyrimidines such as O4-methylthymine, O2-methylcytosine and O 2-methylthymine. We compared the intrinsic properties, such as proton affinities, gas phase acidities, equilibrium tautomerization and nucleobase pair's hydrogen bonding properties, of these... 

We have investigated the pathways of stability for NHCs derived from azole, di-azole, n-tetrazole, and ab-tetrazole (1a, 2a, 3a, and 4a, respectively), at the M06/6-311++G** level of theory. Optimization and vibrational frequency calculations of ground states (GS) and transition states (TS) are performed to identify Gibbs free energies and nature of stationary points, respectively. Two possible pathways of stability for 1a-4a are compared and contrasted which entail dimerization through hydrogen bonding (HB) and covalent bonding (CB). The CB pathway comprises head to head (HH) and head to tail (HT) dimerizations. Plausible reaction profiles are illustrated for 1a-4a along with the mechanism... 

The synthesis of modified versions of deoxyribonucleic acid is an area that is receiving much attention. The replacement of the nitrogen atom on the nucleobases with boron atom has provided insight into deoxyribonucleic acid and ribonucleic acid stability, recognition, and replication at the atomic level. In the present research, we investigated a detailed density functional theory study of the structural, tautomeric, base-pairing ability, bond dissociation energy, and electronic properties of two boron analogues (i.e., boron substitutions at 4-position and 5-position of uracil) of uracil nucleobase. The effects of these modifications on theirs acid-base properties have been considered. Our... 

Herein, functionalized spiro[indoline-3,5′-pyrazolo[1,2-a]pyridazine]-7′-carbonitrile containing two contiguous chiral stereocenters was efficiently synthesized in a satisfactory yield (up to 91% yield) and with excellent diastereoselectivity. We have reached this satisfactory yield by DABCO-catalyzed [3+3] annulation reactions of an isatin N,N′-cyclic azomethine imine 1,3-dipole with a Knoevenagel intermediate in dichloromethane (DCM) as solvent at ambient temperature; this was an entirely new strategy for creating one quaternary stereogenic center at the position-3 of an oxindole structure using an abnormal tandem Michael addition, N-cyclization, and a unique approach via the azomethine... 

Herein, functionalized spiro[indoline-3,5′-pyrazolo[1,2-a]pyridazine]-7′-carbonitrile containing two contiguous chiral stereocenters was efficiently synthesized in a satisfactory yield (up to 91% yield) and with excellent diastereoselectivity. We have reached this satisfactory yield by DABCO-catalyzed [3+3] annulation reactions of an isatin N,N′-cyclic azomethine imine 1,3-dipole with a Knoevenagel intermediate in dichloromethane (DCM) as solvent at ambient temperature; this was an entirely new strategy for creating one quaternary stereogenic center at the position-3 of an oxindole structure using an abnormal tandem Michael addition, N-cyclization, and a unique approach via the azomethine... 

1-Aminophosphonates are valuable compounds with wide range of applications in biological and industry. Various reaction conditions and catalysts have been reported for the synthesis of 1-aminophosphonates via three-component (dialkyl phosphite + aldehyde + amine) or two-component reaction (dialkyl phosphite + imine). Here a solvent-free synthesis of 1-aminophosphonates under very mild reaction conditions is reported. The three-component condensation reactions of dialkyl phosphite, carbonyl compound, and an amine gave 1- aminophosphonates in good to excellent yields under solvent- and catalyst-free conditions at ambient temperature. Hydrophosphorylation of imines in the presence of dialkyl...