Synthesis, Antimicrobial and Antitumor Evaluations of a New Class of Thiazoles Substituted on the Chromene Scaffold

Abstract

Background & Objective: A new series of thiazoles substituted on the chromene scaffold were prepared by facial approaches starting from (E)-1-(2,3-Dihydrochromen-4-ylidene)thiosemicarbazide derivatives (2a,b). The thiosemicarbazides (2a,b) were reacted with a series of α-halo carbonyl compounds to give the corresponding rhodanine analogues and reacted also with C-acetyl-or Cethoxy- N-hydrazonoyl chlorides to afford the corresponding tri- and tetra-substituted hybrid hydrazinyl thiazole substituted chromenes. Methods: The newly synthesized compounds were screened for their in vitro antimicrobial and antitumor activities by agar diffusion method and MTT assay, respectively. Results: The results of the antimicrobial activity revealed that some of the new compounds exhibited excellent activity against pathogenic microorganism; Candida albicans compared with Ciprofloxacin and nystatin, as the reference drugs. : All of the tested compounds exhibited significant cytotoxic activities comparable to that of the reference drug; Doxorubicin® (on HCT116 (colorectal carcinoma human cell line).

Solvent-Free Synthesis, In Vitro and In Silico Studies of Novel Potential 1,3,4-Thiadiazole-Based Molecules against Microbial Pathogens

“…In addition, 3 exhibited three singlet signals at 8.36 and 9.65 ppm for CH-, OH and NH, respectively. Its 13 C-NMR spectrum The 1,3,4-thiadiazoles were also involved in diverse biological applications [12][13][14][15][16] mostly by virtue of the -N double bond and C-S-group. Thiadiazole moieties can act as two-electron donor systems and hydrogen-binding domains.…”

“…Many antibacterial and antiviral drugs were documented to append the 1,3,4-thiadiazole scaffold in their structures (Figure 1). The 1,3,4-thiadiazoles were also involved in diverse biological applications [12][13][14][15][16] mostly by virtue of the -N double bond and C-S-group. Thiadiazole moieties can act as two-electron donor systems and hydrogen-binding domains.…”

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

“…One of the essential structural features of 4H-ch to impart miscellaneous activity is the occurrence of the fold along the oxygen axis. The molecules containing 2H/4H-ch scaffold exhibit noteworthy potency, such as anticancer (Afifi et al, 2017a ; Halawa et al, 2017 ; Elshaflu et al, 2018 ; Elnaggar et al, 2019 ; Luque-Agudo et al, 2019 ), anticonvulsant (Rawat and Verma, 2016 ), antimicrobial (Suvarna et al, 2017 ; Mashhadinezhad et al, 2019 ), anticholinesterase (Tehrani et al, 2019 ), antidiabetic activities (Soni et al, 2019 ), antituberculosis (Zhao et al, 2020 ), and inhibitory activity against monoamine oxidase (MAO) (Takao et al, 2019 ).…”

Green Synthesis of Chromene Congeners via Multi‐Component Reaction and Their Antimicrobial Studies

“…We have many reports in the literature pertaining to chromene analogue compounds describing the synthetic methodologies to afford them and also focusing on their pharmacological profile. [21][22][23][24][25][26] However, our approach is very unique and we successfully built potent pharmacophores (tetrazole and pyridinedione rings) on the benzopyran scaffold to increase the binding interaction of the compounds with the targeted enzyme leading to enhanced antimicrobial activity.…”