13114-95-9Relevant academic research and scientific papers
Synthesis of Five-Membered Cyclic Guanidines via Cascade [3 + 2] Cycloaddition of α-Haloamides with Organo-cyanamides
Wang, Chuan-Chuan,Qu, Ya-Li,Liu, Xue-Hua,Ma, Zhi-Wei,Yang, Bo,Liu, Zhi-Jing,Chen, Xiao-Pei,Chen, Ya-Jing
, p. 3546 - 3554 (2021/02/16)
The convenient preparation of N2-unprotected five-membered cyclic guanidines was achieved through a cascade [3 + 2] cycloaddition between organo-cyanamides and α-haloamides under mild conditions in good to excellent yields (up to 99%). The corresponding cyclic guanidines could be easily transformed into hydantoins via hydrolysis.
Highly Regioselective Iodination of N-Phenylureas with Iodine/Trichloroisocyanuric Acid
Sanabria, Carlos M.,do Casal, Mariana T.,De Souza, Raphael B. A.,De Aguiar, Lúcia C. S.,De Mattos, Marcio C. S.
, p. 1648 - 1654 (2017/03/21)
An efficient regioselective iodination of N-phenylureas was developed using iodine/trichloroisocyanuric acid in acetonitrile at room temperature. This protocol proved to be effective on a broad range of substituted N-phenylureas, forming the p-iodinated compounds in 65-96% yield under mild and neutral conditions.
The impact of modular substitution on crystal packing: The tale of two ureas
Koshti, Vijay S.,Thorat, Shridhar H.,Gote, Ravindra P.,Chikkali, Samir H.,Gonnade, Rajesh G.
, p. 7078 - 7094 (2016/10/03)
A small library of 13 (3a-m) compounds with modular positioning of iodide and urea/thiourea groups was synthesized in excellent yields in a single step synthetic protocol. The existence of the anticipated (thio)urea derivatives was unambiguously establish
Highly Enantioselective Pd-Catalyzed Synthesis of P-Stereogenic Supramolecular Phosphines, Self-Assembly, and Implication
Koshti, Vijay S.,Mote, Nilesh R.,Gonnade, Rajesh G.,Chikkali, Samir H.
supporting information, p. 4802 - 4805 (2015/11/09)
Metal-catalyzed asymmetric addition of a secondary phosphine to an aryl halide is one of the most efficient and reliable approaches for the construction of enantiopure carbon-phosphorus bonds. An isolated Pd(II) complex (5) catalyzes the carbon-phosphorus coupling reaction between tolylphenylphosphine (1a) and 3-iodophenylurea (2b), which proceeds with an unprecedented enantiomeric excess (ee) of 97%. The generality of the strategy has been demonstrated by preparing a small library of a new class of P-stereogenic phosphines with an in-built hydrogen bonding motif for the first time. The P-stereogenic phosphines self-assemble on a metal template via deliberately installed hydrogen-bonding motifs and mimic the bidentate ligand coordination. Interestingly, when it was employed in asymmetric hydrogenation, the supramolecular phosphine {1-(3-(phenyl(o-tolyl)phosphanyl)phenyl)urea} (6b) produced the corresponding hydrogenated product with the highest enantiomeric excess of 99% along with excellent conversion, demonstrating the potential of these enantioenriched P-chirogenic supramolecular phosphines in asymmetric catalysis.
The use of aqueous potassium dichloroiodate for the synthesis of ureas
Viana, Gil Mendes,De Sequeira Aguiar, Lúcia Cruz,De Araújo Ferr?o, Jonas,Simas, Alessandro Bolis Costa,Vasconcelos, Marcela Guariento
, p. 936 - 940 (2013/03/13)
We report a straightforward and efficient reaction protocol for the syntheses of substituted ureas via treatment of thioureas with aqueous potassium dichloroiodate (KICl2). By tuning the reaction condition, thioureas bearing activated N-aryl substituents may undergo either selective oxidation or sequential oxidation and iodination, forming iodoaryl ureas in the latter case.
Design, synthesis, and potential CNS activity of some new bioactive 1-(4-substituted-phenyl)-3-(4-oxo-2-methyl- 4H-quinazolin-3-yl)-urea
Kashaw, Sushil K.,Kashaw, Varsha,Mishra, Pradeep,Jain,Stables
experimental part, p. 738 - 745 (2012/05/20)
Twelve new 1-(4-substituted-phenyl)-3-(4-oxo- 2-methyl-4H-quinazolin-3-yl)- urea were synthesized and screened for anticonvulsant, CNS depressant, and sedativehypnotic activity. After i.p. injection to mice at doses of 30, 100, and 300 mg/kg body weight 2,3-Disubstitutedquinazolin- 4(3H)-one were examined in the maximal electroshock-induced seizures (MES) and subcutaneous pentylenetetrazole (scPTZ) induced seizure models in mice. Spectroscopic data and elemental analysis were consistent with the newly synthesized compounds. The neurotoxicity was assessed using the rotorod method. M3, M4 and M10 were found to be active in both MES screen and scPTZ screen at 0.5 h. All except M11 showed more than 44% decrease in locomotor activity after 1 h of compound administration via actophotometer screen. CNS-depressant activity screened with the help of the forced swim method resulted into some potent compounds. Except for M6 and M11 other tested compounds were found to exhibit potent CNS depressants activity as indicated by increased immobility time. It can be concluded that newly synthesized compounds possessed sedative-hypnotic and CNS depressant activities. Springer Science+Business Media, LLC 2010.
Hybrid calix[4]arenes via ionic hydrogenation and transition-metal-mediated processes
Bew, Sean P.,Brimage, Rebecca A.,Hiatt-Gipson, Glyn,Sharma, Sunil V.,Thurston, Sean
supporting information; experimental part, p. 2483 - 2486 (2009/10/18)
We report the first application of ionic hydrogenation for the synthesis of upper-rim urea- or carbamate-derived hybrid calix[4]arenes. Subsequent metal-mediated transformations using 4-iodophenylurea calixarenes afforded structurally unique 1,3-di(biaryl)-, 1,3-di(biarylalkyne)-, or 1,3-(biaryl)(biarylalkyne)-derived hybrid calixarenes.
Synthesis, anticonvulsant and CNS depressant activity of some new bioactive 1-(4-substituted-phenyl)-3-(4-oxo-2-phenyl/ethyl-4H-quinazolin-3-yl)-urea
Kashaw, Sushil K.,Kashaw, Varsha,Mishra, Pradeep,Jain,Stables
experimental part, p. 4335 - 4343 (2009/12/24)
Several new 1-(4-substituted-phenyl)-3-(4-oxo-2-phenyl/ethyl-4H-quinazolin-3-yl)-urea were synthesized and screened for anticonvulsant, CNS depressant and sedative-hypnotic activity in the mice. After i.p. injection to mice at doses of 30, 100, and 300 mg/kg body weight synthesized compounds were examined in the maximal electroshock induced seizures (MES) and subcutaneous pentylenetetrazole (scPTZ) induced seizure models in mice. Spectroscopic data and elemental analysis were consistent with the newly synthesized compounds. The neurotoxicity was assessed using the rotorod method. Compounds E1, E6, E9, E12, P3, P4 and P6 were found to be active in the MES screen whereas E1, P4, P6 and P11 were found to be active in the scPTZ screen. All except E6, E11 and P6 showed more than 50% decrease in locomotor activity at 1 h of compound administration via actophotometer screen. CNS depressant activity screened with the help of the forced swim method resulted into some potent compounds. All the compounds were found to exhibit potent CNS depressants activity as indicated by increased immobility time. It can be concluded that newly synthesized compounds possessed promising CNS activities.
Synthesis and activity of 1,3,5-triphenylimidazolidine-2,4-diones and 1,3,5-triphenyl-2-thioxoimidazolidin-4-ones: Characterization of new CB 1 cannabinoid receptor inverse agonists/antagonists
Muccioli, Giulio G.,Wouters, Johan,Charlier, Caroline,Scriba, Gerhard K. E.,Pizza, Teresa,Di Pace, Pierluigi,De Martino, Paolo,Poppitz, Wolfgang,Poupaert, Jacques H.,Lambert, Didier M.
, p. 872 - 882 (2007/10/03)
Obesity and metabolic syndrome, along with drug dependence (nicotine, alcohol, opiates), are two of the major therapeutic applications for CB 1 cannabinoid receptor antagonists and inverse agonists. In the present study, we report the synthesis and structure-affinity relationships of 1,5-diphenylimidazolidine-2,4-dione and 1,3,5-triphenylimidazolidine-2,4-dione derivatives. These new 1,3,5-triphenylimidazolidine-2,4-dione derivatives and their thio isosteres were obtained by an original pathway and exhibited interesting affinity and selectivity for the human CB1 cannabinoid receptor. A [35S]-GTPγS binding assay revealed the inverse agonist properties of the compounds at the CB1 cannabinoid receptor. Furthermore, molecular modeling studies were conducted in order to delineate the binding mode of this series of derivatives into the CB1 cannabinoid receptor. 1,3-Bis(4-bromophenyl)-5-phenylimidazolidine-2,4-dione (25) and 1,3-bis(4-chlorophenyl)-5-phenylimidazolidine-2,4-dione (23) are the imidazolidine-2,4-dione derivatives possessing the highest affinity for the human CB1 cannabinoid receptor reported to date.
1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives: New templates among the CB1 cannabinoid receptor inverse agonists
Muccioli, Giulio G.,Wouters, Johan,Scriba, Gerhard K. E.,Poppitz, Wolfgang,Poupaert, Jacques H.,Lambert, Didier M.
, p. 7486 - 7490 (2007/10/03)
New 1-benzhydryl-3-phenylurea derivatives and their 1-benzhydryl-3- phenylthiourea isosteres were synthesized and evaluated for their human CB 1 and CB2 cannabinoid receptor affinity. These compounds proved to be selective CB1 cannabinoid receptor ligands, acting as inverse agonists in a [35S]-GTPγS assay. The affinity of 3,5,5′-triphenylimidazolidine-2,4-dione and 3,5,5′-triphenyl-2- thioxoimidazolidin-4-one derivatives, possessing the 1-benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea moiety, respectively, was also evaluated. In conclusion, the 1-benzhydryl-3-phenylurea scaffold seems to be a new interesting template of CB1 cannabinoid receptor inverse agonists.
