New ferrocenic pyrrolo[1,2-a]quinoxaline derivatives: Synthesis, and in vitro antimalarial activity – Part II

Design, synthesis and antimalarial activity of novel bis{N-[(pyrrolo[1,2-a]quinoxalin-4-yl)benzyl]-3-aminopropyl}amine derivatives

“…These compounds have been reported as key intermediates for the assembly of several heterocycles including antipsychotic agents, anti-HIV agents, adenosine A 3 receptor modulators 19 , antiparasitic agents [20][21][22][23][24][25] and antitumor agents [26][27][28][29][30] . In the course of our work devoted to discover new compounds employed in the antiparasitic chemotherapy, we previously identified some series of substituted pyrrolo[1,2-a]quinoxaline derivatives designed as interesting bioactive isosteres of quinoline derivatives [20][21][22][23][24] .Thus, taking into account our experience in the field of the synthesis of new antimalarial heterocyclic compounds based on our pyrrolo[1,2-a]quinoxaline heterocyclic core [20][21][22][23][24][27][28][29][30] , we decided to incorporate a benzyl group in position 4 of the heterocyclic skeletonof our previously described bispyrrolo [1,2-a]quinoxalines C 20 to broaden the structural diversity of these derivatives, and mainly to increase the aromatic surface of these designed compounds ( Figure 1). …”

An Efficient One-Pot Synthesis of (1,2-Dihydro-2-Oxoquinoxaline-3-Yl)Methyl Carbamodithioate Derivatives From Benzene-1,2-Diamines, Ethyl Bromopyruvate, CS2, and Secondary Amines

“…Quinoline compounds have been found to possess antipsychotic, antitumor, antiparasitic, adenosine A3 receptor modulator, antiviral, anticancer, and anti-inflammatory properties [4][5][6][7][8][9][10][11]. Porter et al recently investigated the quinoxaline scaffold as a template to the design of inhibitors of c-Met kinase [12].…”

Present status of quinoxaline motifs: Excellent pathfinders in therapeutic medicine

“…Recent updates showed that the chemistry of quinoxaline has attracted considerable attention [4] due to its diverse chemical reactivities [5][6][7], application in material science [8,9] and wide spectrum of biological activities [10,11]. Quinoxaline motif is known to represent a class of medicinally important compounds which are effective as antibacterial [1,4], antifungal [2,10], anticancer [11], analgesic [12], antimalarial [13], antitumor [14], antiamoebic [15], antiepileptic [16], anticonvulsant [17], antitubercular [18], antiproliferative [19], anti-HCV [20], anti-inflammatory [21] agents among others. Compounds with quinoxaline cores are used as allosteric dual Akt1 and Akt2 inhibitors, human cytomegalovirus polymerase inhibitors [22], Src-Family Kinase p56Lck inhibitors [23], SRPK-1 inhibitors [24] and monoamine oxidase A inhibitors [25].…”

“…According to Maichrowski and coworkers, ocycloalkylated quinoxaline N-oxide 142 was a new lead compound which possessed reasonable antimalarial activity in vitro without affecting the erythrocytes even at IC 50 of 4.1 + 0.5 µM[140]. Bispyrrolo[1,2-a]quinoxaline 143 exhibited significant antimalarial activity against D10 strains of Plasmodium falciparum[141] while ferrocenic pyrrolo[1,2-a]quinoxaline 144 was active against P. falciparum CQ-sensitive strain F32 (IC 50 = 0.038 + 0.003 µM) as well as the CQ-resistant strains FcB1 (IC 50 = 0.1423 + 0.037 µM) and K1 ((IC 50 = 0.1003 + 0.014 µM)[13]. Based on the review by Kaur and coworkers, 6,7-dinitroquinoxaline 145 was documented…”