3764-01-0Relevant articles and documents
Synthesis of new organochalcogen (Se or Te) based multifunctional pyrimidine derivatives: X-ray structure determination of 2,4- bis(arylchalcogenyl)pyrimidine and 2-chloro-4,6-bis(arylchalcogenyl)pyrimidine compounds
Arora, Ekta,Bhasin,Mehta,Sharma, Nidhi,Bhasin,Jacob, Claus,Félix, Vítor,Neogi, Subhadip
, p. 316 - 322 (2014)
A new class of multinucleate pyrimidine chalcogen (Se/Te) derivatives, i.e. 2,4-bis(arylchalcogenyl)pyrimidine and 2-chloro-4,6-bis(arylchalcogenyl) pyrimidine compounds, has been synthesized for the first time by the nucleophilic substitution of chlorine at the C-2 and C-4 positions of 2,4-dichloropyrimidine and at the C-4 and C-6 positions of 2,4,6- trichloropyrimidine with a variety of chalcogen bearing aryl anions ArE - (Ar = phenyl, 1-naphthyl, p-tolyl). All the newly prepared pyrimidyl chalcogen compounds have been thoroughly characterized with the help of various spectroscopic techniques, viz, NMR (1H, 13C, 77Se), FT-IR and mass spectrometry (in representative cases). The crystal structures of 2,4-bis(naphthalen-1-ylselanyl)pyrimidine (1c), 2,4-bis(phenyltelluryl)pyrimidine (1d), 2-chloro-4,6-bis(phenylselanyl) pyrimidine (2a) and 4,6-bis(p-tolylselanyl)-2-chloropyrimidine (2b) were confirmed by X-ray crystallographic analysis.
Invariant and Variable Supramolecular Self-Assembly in 6-Substituted Uracil Derivatives: Insights from X-ray Structures and Quantum Chemical Study
Abdelbaky, Mohammed S. M.,Al-Wahaibi, Lamya H.,Bysani, Sai Ramya Sree,El-Emam, Ali A.,Garcia-Granda, Santiago,Percino, M. Judith,Tawfik, Samar S.,Thamotharan, Subbiah
, p. 3234 - 3250 (2021/05/29)
In this study, three new 6-(arylthio)uracil derivatives, namely, 6-(phenylthio)pyrimidine-2,4(1H,3H)-dione (1), C10H8N2O2S; 6-(p-tolylthio)pyrimidine-2,4(1H,3H)-dione (2), C11H10N2O2S; and 6-(3,5-dimethylphenylthio)pyrimidine-2,4(1H,3H)-dione (3), C12H12N2O2S, have been synthesized. Single-crystal structures of these compounds reveal an invariant molecular tape contains alternate R22(8) synthons formed by N-H···O hydrogen bonds in 1 and 3. This alternate hydrogen-bonded pattern disappeared in 2; instead, a new synthon is generated. The lattice energy calculation suggests that the methyl-substituted derivatives (2 and 3) have high stabilization energy than compound 1. The electrostatic potential map reveals the difference in the accepting tendency of the carbonyl oxygen. The Hirshfeld surface and 2D-fingerprint plots analyses demonstrate that the major intermolecular interactions come from H···O contacts in 1, and these contacts were reduced due to the presence of methyl substitutions in 2 and 3. This reduction is compensated by the increase of the same amount of H···H contacts in these structures. Further, the PIXEL energy and DFT calculations at the M06-2X-D3/cc-pVTZ level of theory were used to characterize the dimeric topology formed in structures of 1-3. The intermolecular interaction energies of dimers calculated by the PIXEL method were compared with the B97D3/def2-TZVP level of approximation. Although these molecules' crystal packing is somewhat different, the energy frameworks show similarities on the respective crystal structure's shortest axis. Furthermore, the nature and strength of various noncovalent interactions such as N-H···O, C-H···O/S/π, π···π, and a chalcogen bond of type C-S···O═C were evaluated using the Bader's quantum theory of atoms-in-molecules framework.
Diverse combinatorial design, synthesis and in vitro evaluation of new HEPT analogues as potential non-nucleoside HIV-1 reverse transcription inhibitors
Puig-De-La-Bellacasa, Raimon,Gimenez, Laura,Pettersson, Sofia,Pascual, Rosalia,Gonzalo, Encarna,Este, Jose A.,Clotet, Bonaventura,Borrell, Jose I.,Teixido, Jordi
experimental part, p. 159 - 174 (2012/09/05)
New analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) were synthesized and evaluated for their in vitro activities against HIV-1 in MT-4 cell cultures. Chemical diversity was introduced in 4 of the six positions of the core and the influence of each substituent was studied. This library was built on the basis of a rational diversity analysis with the objective of maximizing diversity and thus, the activity range with a minimum number of synthesized compounds. Among them, 2{1,2,3,1} and 2{1,2,3,4} exhibited the most potent anti-HIV-1 activities (EC50 = 0.015 μg/mL; 0.046 μM, SI >1667) and (EC50 = 0.025 μg/mL; 0.086 μM, SI >1000), respectively, which were about 71-fold and 38-fold more active than the reference compound HEPT (EC50 = 1.01 μg/mL; 3.27 μM, SI >25).
