The reduction of nitroarenes is the main methodology to produce anilines, important precursors of building blocks, dyes, and drugs. Continuing our goal of describing sustainable methodologies for the reduction of nitroarenes to their respective anilines, herein we compile selected reaction protocols, using organic medium, reported from 2017 to 2023, in order to provide a comprehensive and complementary view of the new processes and catalysts developed during this period. anilines blocks dyes drugs protocols medium 201 2023 period 20 202 2

This work describes the multigram-scale synthesis of the building-block N1 (7 chloroquinolin-4-yl)ethane-1,2-diamine via sonochemistry and its use in the synthesis of seven new quinoline-thiazole hybrids endowed with interesting anticancer activity. Target compounds were planned based on the drugs chloroquine and primaquine and the desired thiazoles were obtained through the Hantzsch thiazole synthesis, without the use of catalysts, by reacting key intermediate 1-(2-((7-chloroquinolin-4-yl)amino)ethyl)thiourea, obtained in two-steps from N1 (7-chloroquinolin-4-yl)ethane-1,2-diamine, with different 2-bromoacetophenones. The novel molecules were assessed against four different leukemia cell lines (HL60, K562, KASUMI-1, and KG-1) plus normal fibroblasts (L929), using the 3-(4,5-dimethyl-2-thiazol)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, and showed, overall, a high cytotoxic profile, but with interesting selectivity index, especially against K562 cells (1.89 to 5.50), when compared to standard doxorubicin (3.51). Docking studies suggest that all tested derivatives are able to interact with BCR-ABL1 tyrosine kinase enzyme, and, therefore, these molecules may be promising leads against chronic myeloid leukemia. multigramscale multigram scale buildingblock building block N 7 ( chloroquinolin4ylethane1,2diamine chloroquinolin4ylethane12diamine chloroquinolinylethanediamine chloroquinolin 4 yl ethane 1,2 diamine 1 2 quinolinethiazole quinoline activity catalysts 127chloroquinolin4ylaminoethylthiourea, 127chloroquinolin4ylaminoethylthiourea chloroquinolinylaminoethylthiourea amino ethyl thiourea, thiourea 1-(2-((7-chloroquinolin-4-yl)amino)ethyl)thiourea twosteps two steps 7chloroquinolin4ylethane1,2diamine, 7chloroquinolin4ylethane12diamine diamine, (7-chloroquinolin-4-yl)ethane-1,2-diamine 2bromoacetophenones. 2bromoacetophenones bromoacetophenones bromoacetophenones. 2-bromoacetophenones HL60, HL60 HL (HL60 K KASUMI1, KASUMI1 KASUMI 1, KASUMI-1 KG1 KG KG-1 L929, L929 L , (L929) 34,5dimethyl2thiazol2,5diphenyl2Htetrazolium 345dimethyl2thiazol25diphenyl2Htetrazolium dimethylthiazoldiphenylHtetrazolium 3 4,5 dimethyl thiazol 2,5 diphenyl 2H tetrazolium 5 H MTT (MTT assay showed overall profile index K56 1.89 189 89 (1.8 5.50, 550 5.50 50 5.50) 3.51. 351 3.51 . 51 (3.51) BCRABL1 BCRABL BCR ABL1 ABL BCR-ABL enzyme therefore chloroquinolin4ylethane1 2diamine ylethane 12 ylaminoethylthiourea 7chloroquinolin4ylethane1 7chloroquinolin4ylethane1,2diamine HL6 (HL6 KASUMI- KG- L92 (L929 34 5dimethyl2thiazol2 5diphenyl2Htetrazolium Htetrazolium 45 4, 25 2, K5 1.8 18 8 (1. 55 5.5 35 3.5 (3.51 chloroquinolinylethane chloroquinolin4ylethane 7chloroquinolin4ylethane (HL L9 (L92 dimethylthiazol 5dimethyl2thiazol diphenylHtetrazolium 1. (1 5. 3. (3.5 (L9 (3. (L (3

Aromatic amines are important intermediates in the industry to produce a wide array of products, and the reduction of aromatic nitro compounds is the main methodology for their preparation. Considering this fact, the objective of this review is to describe the development of sustainable methodologies for the reduction of aromatic nitro compounds for their respective amines from 2017 to 2020. Thus, throughout the text, the reaction conditions and the various reagents, solvents and catalysts used in the synthesis of aromatic amines are presented, along with the main advantages of the methodologies described.

A rapid decrease in parasitaemia remains the major goal for new antimalarial drugs and thus, in vivo models must provide precise results concerning parasitaemia modulation. Hydroxyethylamine comprise an important group of alkanolamine compounds that exhibit pharmacological properties as proteases inhibitors that has already been proposed as a new class of antimalarial drugs. Herein, it was tested the antimalarial property of new nine different hydroxyethylamine derivatives using the green fluorescent protein (GFP)-expressing Plasmodium bergheistrain. By comparing flow cytometry and microscopic analysis to evaluate parasitaemia recrudescence, it was observed that flow cytometry was a more sensitive methodology. The nine hydroxyethylamine derivatives were obtained by inserting one of the following radical in the para position: H, 4Cl, 4-Br, 4-F, 4-CH3, 4-OCH3, 4-NO2, 4-NH2 and 3-Br. The antimalarial test showed that the compound that received the methyl group (4-CH3) inhibited 70% of parasite growth. Our results suggest that GFP-transfected P. berghei is a useful tool to study the recrudescence of novel antimalarial drugs through parasitaemia examination by flow cytometry. Furthermore, it was demonstrated that the insertion of a methyl group at the para position of the sulfonamide ring appears to be critical for the antimalarial activity of this class of compounds.