Design, Synthesis and Antimalarial Activity of Some New Aminoalcoholpyrrolo[1,2-a]quinoxaline Derivatives

1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one: Synthesis, Crystal Structure and Anti-Leukemic Activity

“…The Clauson-Kaas reaction of 2-nitroaniline 1 with 2,5-dimethoxytetrahydrofuran (DMTHF) in acetic acid gave the pyrrolic derivative 2, which was then reduced using a NaBH 4 -CuSO 4 system to provide the attempted 1-(2-aminophenyl)pyrrole 3. The reaction of 3 with triphosgene in refluxing toluene gave the lactam 4, which was subsequently chlorodehydroxylated with phosphorous oxychloride (POCl 3 ), leading to the 4-chloroquinoxaline 5 [6][7][8]11]. This methodology in the access to this pyrrolo[1,2-a]quinoxaline three-cycle skeleton 4 was found more efficient than those previously described [17][18][19].…”

“…Among them, the pyrrolo[1,2-a]quinoxaline heterocyclic moiety has been characterized with respect to a broad range of pharmacological properties [1,2]. Derivatives of this tricyclic system have been previously described as antiprotozoal agents (antimalarial, antitrypanosomal, and antileishmanial), antipsychotic agents, antiviral agents, adenosine receptor modulators, and anticancer agents [3][4][5][6][7][8][9][10][11][12]. The discovery of new anti-cancer molecules is one of the most important goals in pharmaceutical chemistry.…”

“…In this context, and as an extension of our work on the development of new anticancer heterocyclic drugs, we decided to further modulate and substitute our pyrrolo[1,2-a]quinoxaline heterocyclic pharmacophore. Thus, taking into account the experience of our group in the field of the synthesis of new bioactive heterocyclic derivatives based on this pyrrolo[1,2-a]quinoxaline heterocyclic core [6][7][8][9][10][11][12][13][14], we use our previously described anti-leukemic JG454 pyrrolo[1,2-a]quinoxaline moiety ( Figure 1) [15] as a template for the design of a new derivative in which the 4-(2-ketobenzimidazolin-1-yl)piperidine was replaced by the 1-phenyl-1,3,8-triazaspiro [4.5]decan-4-one, a new piperidyl structural analogue.…”

Synthesis and Antiproliferative Effect of Ethyl 4‐[4‐(4‐Substituted Piperidin‐1‐yl)]benzylpyrrolo[1,2‐a]quinoxalinecarboxylate Derivatives on Human Leukemia Cells

“…In the recent years, pyrrolo[1,2‐ a ]quinoxalines have attracted persistent interest due to practically important properties of some their derivatives, specifically, pronounced biological activities. Thus, these heterocyclic derivatives have many biological activities and have been found in many pharmaceutical molecules, including antipsychotic agents, antiviral agents, adenosine receptor modulators, antiparasitic agents, and anticancer agents . The discovery of new therapeutic agents against cancer is one of the most important goals in medicinal chemistry.…”

Synthesis and Antioxidant Evaluation of Quinoxalino[2′,3′:5,6][1,3,4]thiadiazino[2,3‐b]quinazolin‐15‐ones: Derivatives of a Novel Ring System

“…Quinoxalines are core units in a number of medicines with diverse properties like anticancer , antibacterial , antiviral , anti‐HIV , and anti‐inflammatory . Moreover, scientists have already determined many therapeutic activities of quinazolines including antibacterial , antivirus , anti‐cytotoxin , anticancer , antimalarial , anti‐spasm , anti‐inflammation , and others. From the synthetic point of view, treatment of 4‐amino‐1,2,4‐triazole‐3‐thiols with 2,3‐dichloroquinoxalines in refluxing ethanol or in the presence of sodium acetate under microwave irradiation can afford the bioactive [1,2,4]triazolo‐thiadiazino[5,6‐ b ]quinoxalines.…”