77557-02-9Relevant articles and documents
Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source
Qi, Xinxin,Zhou, Rong,Peng, Jin-Bao,Ying, Jun,Wu, Xiao-Feng
, p. 5161 - 5164 (2019/01/25)
A selenium-catalyzed carbonylative reaction for the synthesis of 2-benzimidazolones from 2-nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene-1,3,5-triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2-benzimidazolones were produced in moderate to excellent yields.
Rational Design, Pharmacomodulation, and Synthesis of Dual 5-Hydroxytryptamine 7 (5-HT7)/5-Hydroxytryptamine 2A (5-HT2A) Receptor Antagonists and Evaluation by [18F]-PET Imaging in a Primate Brain
Deau, Emmanuel,Robin, Elodie,Voinea, Raluca,Percina, Nathalie,Sata?a, Grzegorz,Finaru, Adriana-Luminita,Chartier, Agnès,Tamagnan, Gilles,Alagille, David,Bojarski, Andrzej J.,Morisset-Lopez, Séverine,Suzenet, Franck,Guillaumet, Gérald
, p. 8066 - 8096 (2015/11/09)
We report the synthesis of 46 tertiary amine-bearing N-alkylated benzo[d]imidazol-2(3H)-ones, imidazo[4,5-b]pyridin-2(3H)-ones, imidazo[4,5-c]pyridin-2(3H)-ones, benzo[d]oxazol-2(3H)-ones, oxazolo[4,5-b]pyridin-2(3H)-ones and N,N′-dialkylated benzo[d]imidazol-2(3H)-ones. These compounds were evaluated against 5-HT7R, 5-HT2AR, 5-HT1AR, and 5-HT6R as potent dual 5-HT7/5-HT2A serotonin receptors ligands. A thorough study of the structure-activity relationship of the aromatic rings and their substituents, the alkyl chain length and the tertiary amine was conducted. 1-(4-(4-(4-Fluorobenzoyl)piperidin-1-yl)butyl)-1H-benzo[d]imidazol-2(3H)-one (79) and 1-(6-(4-(4-fluorobenzoyl)piperidin-1-yl)hexyl)-1H-benzo[d]imidazol-2(3H)-one (81) were identified as full antagonist ligands on cyclic adenosine monophosphate (cAMP, KB = 4.9 and 5.9 nM, respectively) and inositol monophosphate (IP1, KB = 0.6 and 16 nM, respectively) signaling pathways of 5-HT7R and 5-HT2AR. Both antagonists crossed the blood-brain barrier as evaluated with [18F] radiolabeled compounds [18F]79 and [18F]81 in a primate's central nervous system using positron emission tomography. Both radioligands showed standard uptake values ranging from 0.8 to 1.1, a good plasmatic stability, and a distribution consistent with 5-HT7R and 5-HT2AR in the CNS.
Highly efficient synthesis of ureas and carbamates from amides by iodosylbenzene-induced hofmann rearrangement
Liu, Peng,Wang, Zhiming,Hu, Xianming
experimental part, p. 1994 - 2000 (2012/05/05)
A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. Symmetric and asymmetric ureas and carbamates can be prepared by this procedure in up to 98 % yield. Ureidopeptides can also be prepared in good yield by this method. A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. By using this method, heterocyclic products can be easily obtained in excellent yield. Ureidopeptides can also be prepared in good yield by this procedure. Copyright
Towards the synthesis of new benzimidazolone derivatives with surfactant properties
Lakhrissi, Brahim,Benksim, Abdelhafid,Massoui, Mohamed,Essassi, El Mokhtar,Lequart, Vincent,Joly, Nicolas,Beaupere, Daniel,Wadouachi, Anne,Martin, Patrick
, p. 421 - 433 (2008/09/19)
New water-soluble benzimidazolone derivatives were synthesized. In the first approach, di-N-glycosyl and mono-N-alkyl-N-glycosyl compounds were obtained by grafting C-6-activated glycosides onto benzimidazolone. In the second approach, benzimidazolone der
Copper-catalyzed intramolecular N-arylation of ureas in water: a novel entry to benzoimidazolones
Barbero, Nekane,Carril, Mónica,SanMartin, Raul,Domínguez, Esther
, p. 7283 - 7288 (2008/09/21)
The copper-catalyzed intramolecular N-arylation of 2-bromoarylureas performed in water leading to the benzo[d]imidazolone framework is reported. The scope of the methodology presented herein proved to?be broad and afforded a significant number of benzoimidazolones in good to excellent yields. The reported protocol is based on the use of CuI and TMEDA acting both as the ligand and as the base in a water solution, which allows for the easy separation of the catalyst containing aqueous phase from the products by simple extraction. Additionally, the N- versus O-arylation competitive processes are also discussed.
Hypervalent iodine oxidative rearrangement of anthranilamides, salicylamides and some β-substituted amides: A new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and related compounds
Prakash,Batra,Kaur,Sharma,Sharma,Singh,Moriarty
, p. 541 - 543 (2007/10/03)
Oxidation of anthranilamides, salicylamides and some β-substituted amides with iodobenzene diacetate in methanolic potassium hydroxide led to a new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and related compounds, respectively. The reaction probably occurs via initial Hofmann-type rearrangement followed by intramolecular cyclization of intermediate isocyanate.
2,3-dihydro-2-oxo-1H-benzimidazole-1-carboxamides with selective affinity for the 5-HT4 receptor: Synthesis and structure-affinity and structure-activity relationships of a new series of partial agonist and antagonist derivatives
Tapia, Inés,Alonso-Cires, Luisa,López-Tudanca, Pedro Luis,Mosquera, Ramón,Labeaga, Luis,Innerárity, Ana,Orjales, Aurelio
, p. 2870 - 2880 (2007/10/03)
A series of 2,3-dihydro-2-oxo-1H-benzimidazole-l-carboxamide derivatives bearing a piperazine moiety was synthesized. Their in vitro 5-HT4, 5-HT3, and D2 receptors affinities were evaluated by radioligand binding assay. For selected compounds functional studies at the 5-HT4 receptor were made by using precontracted (by carbachol) preparations of rat esophageal tunica muscularis mucosae (TMM). The influence of the 3-substituent of the benzimidazole ring, the 4-substituent of the piperazine moiety, and the alkylene spacer was studied. Compounds with an ethyl or a cyclopropyl substituent in the 3-position of the benzimidazole ring showed moderate to high affinity (K(i) = 6.7-75.4 nM) for the 5-HT4 receptor with selectivity over 5-HT3 and D2 receptors and moderate antagonist activity (pK(b) = 6.19- 7.73). Compounds with an isopropyl substituent in the 3-benzimidazole position exhibited moderate and selective 5-HT4 affinity (K(i) ≥ 38.9 nM) and a partial agonist activity (5a, i.a. = 0.94) higher than that of the reference compound BIMU 8 (i.a. = 0.70). This reversal of the pharmacological activity due only to a small structural difference might confirm the existence of two binding sites on the 5-HT4 receptor. In the alkylene spacer, a two-methylene chain is favorable to optimize the affinity and the antagonist or the partial agonist activity. In the ethyl and cyclopropyl series, 5-HT4 antagonist activity seems to be unrelated to the size of the 4-substituent of the piperazine moiety, whereas a methyl group is optimal for high partial agonist activity in the isopropyl series; however, the presence of a butyl substituent is a favorable pattern for 5-HT4 antagonism and even causes a reversal of the pharmacological profile in the isopropyl series (5h, pK(b) = 7.94). N-Butyl quaternization of 5a led to an improvement in affinity for the 5-HT4 receptor and maintained the high partial agonist activity (5r, K(i) = 66.3 nM, i.a. = 0.93).
Synthesis of 1-Alkyl and 1,3-Dialkyl-2-benzimidazolones from 1-Alkenyl-2-benzimidazolones using Phase-Transfer Catalysts Technique
Vernin, Gaston,Domlog, Hicham,Siv, Chan,Metzger, Jaques,El-Shafei, Ahmed Kamal
, p. 85 - 89 (2007/10/02)
A general synthetic route to 1-alkyl and 1,3-dialkyl-2-benzimidazolones from 1-alkenyl-2-benzimidazolenes using phase-transfer catalysis conditions is described.
