856850-57-2Relevant academic research and scientific papers
Air-Stable Pd Catalytic Systems for Sequential One-Pot Synthesis of Challenging Unsymmetrical Aminoaromatics
Shaya, Janah,Deschamps, Marie-Angélique,Michel, Beno?t Y.,Burger, Alain
, p. 7566 - 7573 (2016/09/09)
The selective functionalization of dibromoaromatic scaffolds using air-stable palladium catalytic systems was carried out. This methodology involved rapid mono and diselective Buchwald-Hartwig aminations via microwave irradiation. The conditions were optimized to couple sequentially different moieties in one pot. Couplings with a wide scope of amines allowed accessing a new library of symmetrical and unsymmetrical derivatives (35 examples). Using this versatile method, a near-IR push-pull sensor was prepared installing the electron-donating and -withdrawing groups through a multicomponent reaction. These conditions revealed to be gram-scalable and adaptable to various groups; hence, promoting facile use in synthetic chemistry.
Diarylureas as allosteric modulators of the cannabinoid CB1 receptor: Structure-activity relationship studies on 1-(4-chlorophenyl)-3-{3-[6-(pyrrolidin-1-yl)pyridin-2-yl]phenyl}urea (PSNCBAM-1)
German, Nadezhda,Decker, Ann M.,Gilmour, Brian P.,Gay, Elaine A.,Wiley, Jenny L.,Thomas, Brian F.,Zhang, Yanan
, p. 7758 - 7769 (2015/01/08)
The recent discovery of allosteric modulators of the CB1 receptor including PSNCBAM-1 (4) has generated significant interest in CB1 receptor allosteric modulation. Here in the first SAR study on 4, we have designed and synthesized a series of analogs focusing on modifications at two positions. Pharmacological evaluation in calcium mobilization and binding assays revealed the importance of alkyl substitution at the 2-aminopyridine moiety and electron deficient aromatic groups at the 4-chlorophenyl position for activity at the CB1 receptor, resulting in several analogs with comparable potency to 4. These compounds increased the specific binding of [3H]CP55,940, in agreement with previous reports. Importantly, 4 and two analogs dose-dependently reduced the Emaxof the agonist curve in the CB1 calcium mobilization assays, confirming their negative allosteric modulator characteristics. Given the side effects associated with CB1 receptor orthosteric antagonists, negative allosteric modulators provide an alternative approach to modulate the pharmacologically important CB1 receptor.
Regioselective intramolecular electrophilic substitution reactions involving π-deficient pyridine substrates: a new entry to pyridoquinazolines and benzo[h][1,6]naphthyridines
Agarwal, Piyush K.,Saifuddin, Mohammad,Kundu, Bijoy
experimental part, p. 862 - 870 (2010/03/25)
Regioselective intramolecular electrophilic substitution reactions have been described in π-deficient pyridine substrates tethered at C-2 to the aryl amine. The presence and nature of ring activating groups at C-6 led to the involvement of either N-1 or C-3 of the pyridine ring in the cyclization thereby leading to the regioselective synthesis of pyridoquinazolines and naphthyridines in excellent yields.
