4777-48-4Relevant academic research and scientific papers
Synthesis, molecular structure optimization, and cytotoxicity assay of a novel 2-acetyl-3-amino-5- [(2-oxopropyl)sulfanyl]-4-cyanothiophene
Mabkhot, Yahia N.,Aldawsari, Fahad D.,Al-Showiman, Salim S.,Barakat, Assem,Soliman, Saied M.,Choudhary, Muhammad I.,Yousuf, Sammer,Hadda, Taibi Ben,Mubarak, Mohammad S.
, (2016)
A novel thiophene-containing compound, 2-acetyl-3-amino-5-[(2-oxopropyl)sulfanyl]-4- cyanothiophene (4) was synthesized by reaction of malononitrile with CS2 in the presence of K2CO3 under reflux in DMF and the subsequent reaction with chloroacetone followed by cyclization. This compound has been characterized by means of FT-IR, 1H-NMR, 13C-NMR, and mass spectrometry as well as elemental analysis. In addition, the molecular structures of compound 4 was determined by X-ray crystallography. The geometry of the molecule is stabilized by an intramolecular interaction between N1-H1? O1 to form S6 graf set ring motif. In the crystal, molecules are linked via N1-H2? O1 and C7-H7A?N2 interactions to form a three-dimensional network. Molecular structure and other spectroscopic properties of compound 4 were calculated using DFT B3LYP/6-31G (d,p) method. Results revealed a good agreement between the optimized geometric parameters and the observed X-ray structure. Furthermore, and by employing the natural bond orbital (NBO) method, the intramolecular charge transfer (ICT) interactions along with natural atomic charges at different sites, were calculated; results indicated strong n=π? ICT from LP(1)N5?BD?(2)C15-C16 (63.23 kcal/mol). In addition, the stabilization energy E(2) of the LP(2)O3→BD?(1)N5-H6 ICT (6.63 kcal/mol) indicated the presence of intramolecular N-H?OH bonding. Similarly, calculations of the electronic spectra of compound 4 using, TD-DFT revealed a good agreement with the experimental data. Finally, compound 4 was evaluated for its in vitro cytotoxic effect against PC-3 and HeLa cell lines, as an anticancer agent, and found to be nontoxic.
Synthesis of (5aS)-2-benzylthio-3-cyano-4,5a,6,7,8,10-hexahydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-5,10-diones
Fedorov,Rodinovskaya,Shestopalov,Sigeev
, p. 394 - 405 (2021)
A convenient method was developed for the combinatorial synthesis of substituted (5aS)-2-benzylthio-3-cyano-4,5a,6,7,8,10-hexahydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]-diazepine-5,10-diones. The structure and the most probable conformation of (5aS)-2-benzylthio-3-cyano-4,5a,6,7,8,10-hexahydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-5,10-dione in solution was established by NMR spectroscopy and calculations using the Gaussian program.
Comparative evaluation of trace heavy metal ions in water sample using complexes of dithioligands by flame atomic absorption spectrometry
Maurya, Vinay Kumar,Singh, Ravi Pratap,Prasad, Lal Bahadur
, p. 100 - 109 (2018/03/21)
Four new complexes were prepared by the metathetic reaction of trace heavy metals like Cd, Zn, Cu and Hg with two different dithioligands of the formula ML2 [M= Cd, Zn, Cu and Hg and L= potassium-1,1-dicyano-2,2-ethylenedithiolate and potassium
Synthetic method for cefotetan side chain
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Paragraph 0028; 0029; 0030; 0031; 0032, (2019/01/08)
The invention relates to a synthetic method for a cefotetan side chain. Malononitrile and carbon disulfide are used as raw materials. The synthetic route is as follows. The synthetic method has the advantages that raw materials are general, no unpopular chemical material is included, no special and dangerous chemical reaction exists, the reaction condition is mild, the reaction conditions of hightemperature, high pressure, deep cold, and the like, are not required, the raw materials are popular so that the preparation cost is low, the yield is at a higher level and can reach up to above 83% and the synthetic method can meet domestic and oversea supply requirements.
Synthesis of 2,5-asymmetrically substituted 3,4-diaminothieno[2,3- b ]thiophenes by domino reaction
Zubarev, Andrey A.,Larionova, Natalia A.,Rodinovskaya, Lyudmila A.,Mortikov, Valery Yu.,Shestopalov, Anatoliy M.
supporting information, p. 546 - 550 (2013/11/06)
A convenient one pot synthesis of 2,5-asymmetrically substituted thieno[2,3-b]thiophenes is developed. The method is based on consecutive domino reactions (SN2 reaction → Thorpe-Ziegler reaction) using malononitrile and carbon disulfide as starting materials with the generation of potassium 2,2-dicyanoethene-1,1-bis(thiolate) in a solution. The high yield of the target thienothiophenes was achieved using the Ziegler dilution effect.
Copper-catalyzed synthesis of 2H-thiopyran derivatives from alkynes, sulfonyl azides, carbon disulfide, and malononitrile
Yavari, Issa,Nematpour, Manijeh,Tavakoli, Ziba
, p. 2141 - 2146 (2013/12/04)
A one-pot synthesis of functionalized thiopyran derivatives via a Cu-catalyzed multicomponent reaction of sulfonyl azides, arylacetylenes and dipotassium 2,2-dicyanoethylene-1,1-dithiolate, generated from malononitrile and CS2, has been develop
Facile method for the synthesis of pyrazolo[3,4-b]-pyrido[4,3-d]- pyrimidine-4-ones via a tandem aza-wittig reaction
Wang, Tao,Zheng, Cai Hua,Liu, Shu,He, Hong Wu
supporting information; scheme or table, p. 3386 - 3398 (2009/12/09)
Fifteen novel pyrazolo[3,4-b]-pyrido[4,3-d]-pyrimidine-4-ones (7a-o) were designed and have been successfully synthesized via tandem aza-Wittig and annulation reactions of the corresponding iminophosphorances 5, phenylisocyanate, and substituted phenols in 60-77% isolated yields. Their structures were clearly verified by infrared (IR), 1H NMR, electron impact-mass spectrometry (EI-MS), and elemental analysis. The results of a preliminary bioassay indicated that some compounds possess inhibition activities against the root of Brassica napus (rape) and Echinochloa crusgalli (barnyard grass) at a dosage of 100mg/L and 10mg/L.
