Synthesis, molecular docking, antiproliferative, and antimicrobial activity of novel pyrano[3,2-c]carbazole derivatives

Reddy, P. N.; Padmaja, P.; Reddy, Bobbala Ramana; Gundla, Rambabu; Kumar, Machiraju Pavan

doi:10.1007/s00044-016-1676-x

Cited by 22 publications

(3 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…After screening, only compound 30f showed superior growth inhibition against MRSA (N315) with an MIC value of 4 μg/mL, whereas the reference drug chloromycin gave a MIC value of 64 μg/mL, and norfloxacin gave 8 μg/mL. Similarly, Narayana et al reported a neat synthesis and antimicrobial activity of 10 new pyrano [3,2- c ]carbazole derivatives ( 31a-e , and 32a-e ) [ 50 ]. In addition to the antiproliferative activity of these 10 adducts, the MIC of each product was obtained for three Gram-positive bacteria, B. subtilis, S. aureus, and S. epidermidis, and three Gram-negative bacteria, P. aeruginosa , K. pneumonia , and E. coli, with penicillin and streptomycin used as the standard drugs.…”

Section: Antibacterial and Antifungal Activities Of Carbazole Derivat...mentioning

confidence: 99%

“…Most of the compounds showed poor antibacterial activity, with only a couple showing moderate to good activity against P. aeruginosa and S. aureus . Carbazole 32b exhibited good activity against P. aeruginosa with an MIC value of 9.37 μg/mL, which is superior in comparison to penicillin (MIC = 12.5 μg/ML) [ 50 ]. Winther et al synthesized 15 N -substituted carbazole derivatives ( 33a-d , 34a-d , and 35a-g ), as depicted in Figure 6 .…”

Section: Antibacterial and Antifungal Activities Of Carbazole Derivat...mentioning

confidence: 99%

See 1 more Smart Citation

Carbazole Derivatives as Potential Antimicrobial Agents

Patil

Blé-González

et al. 2022

Molecules

View full text Add to dashboard Cite

Microbial infection is a leading cause of death worldwide, resulting in around 1.2 million deaths annually. Due to this, medicinal chemists are continuously searching for new or improved alternatives to combat microbial infections. Among many nitrogen-containing heterocycles, carbazole derivatives have shown significant biological activities, of which its antimicrobial and antifungal activities are the most studied. In this review, miscellaneous carbazole derivatives and their antimicrobial activity are discussed (articles published from 1999 to 2022).

show abstract

Section: Antibacterial and Antifungal Activities Of Carbazole Derivat...mentioning

confidence: 99%

Section: Antibacterial and Antifungal Activities Of Carbazole Derivat...mentioning

confidence: 99%

Carbazole Derivatives as Potential Antimicrobial Agents

Patil

Blé-González

et al. 2022

Molecules

View full text Add to dashboard Cite

show abstract

“…Recently, we have developed a simple and efficient one-pot synthetic approach to pyrano [3,2-c]carbazole derivatives [38]. We also reported another approach for the synthesis of novel pyrano [3,2-c]carbazole derivatives via domino Knoevenagel-hetero-Diels-Alder reaction [39,40]. These derivatives showed significant anticancer activity by inhibiting tubulin polymerization.…”

mentioning

confidence: 99%

Microwave Assisted One-Pot Three-Component Synthesis of Novel Pyranocarbazole Derivatives as Antiproliferative Agents and Molecular Docking Studies

Reddy

2019

Asian J. Chem.

Self Cite

View full text Add to dashboard Cite

A new series of pyrano[3,2-c]carbazole and pyrano[2,3-a]carbazole derivatives have been synthesized by one-pot three-component coupling of 4-hydroxycarbazole or 2-hydroxycarbazole, aromatic substituted aldehydes and (E)-N-methyl-1-(methylthio)-2-nitroethenamine under microwave irradiation. This transformation presumably occurs via Knoevenagel condensation-Michael addition–tautomerism intramolecular O-cyclization-elimination sequence of reactions creating one C-O bond and two C-C bonds. The significant features of this one-pot reaction include catalyst free, solvent free, atom-economy, no column chromatographic purification, short reaction time and good yield. Further, the synthesized pyranocarbazole derivatives were evaluated for their antiproliferative activity against four cancer cell lines such as DU 145 (prostate cancer), MDA-MB-231 (breast cancer), SKOV3 (ovarian cancer) and B16-F10 (skin cancer). The results clearly demonstrated that trimethoxyphenyl substituted pyrano[3,2-c]carbazole (9h) exhibited most potent antriproliferative activity against tested cell lines. Compounds 9a, 9b and 11a were also displayed pronounced antriproliferative activity. In addition, molecular docking studies revealed that the lead compounds bind to the colchicine binding site of the tubulin effectively.

show abstract

Synthesis of novel [1,2,3]triazolo[4′,5′:3,4]pyrrolo[1,2‐a]thieno[2,3‐d] pyrimidines: Potent EGFR targeting anti‐breast cancer agents

Samala,

Bapuram

et al. 2024

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

In this study, we designed and synthesized several novel fused [1,2,3]triazolo [4′,5′:3,4]pyrrolo[1,2‐a]thieno[2,3‐d]pyrimidine derivatives using in a single [3 + 2] reaction cycloaddition reaction of 3‐(3‐iodoprop‐2‐yn‐1‐yl)thieno[2,3‐d]pyrimidin‐4(3H)‐one (4) followed by C‐C bond coupling with various aryl azides in a PEG‐400 medium. All of the newly synthesized compounds were evaluated in vitro for EGFR kinase inhibitory action as well as anti‐breast cancer activity against MDA‐MB‐231 and MCF‐7 breast cancer cell lines. When compared to the reference molecule, erlotinib, the majority of the compounds demonstrated adequate efficacy. The most promising compounds, 5g and 5i, demonstrated excellent anticancer activity against both cancer cell lines, with IC50 values ranging from 04.17 ± 0.55 to 8.65 ± 0.89 μM, respectively, as well as excellent kinase inhibitory activities (EGFR: IC50 = 0.467 ± 0.063 and 0.412 ± 0.081 μM). The in silico studies of five potent compounds 5f, 5g, 5h, 5i, and 5k were also carried out to identify the interactions against the EGFR receptor and found that the energy calculations were covenant with the obtained IC50 values.

show abstract

Synthesis, molecular docking, antiproliferative, and antimicrobial activity of novel pyrano[3,2-c]carbazole derivatives

Cited by 22 publications

References 37 publications

Carbazole Derivatives as Potential Antimicrobial Agents

Carbazole Derivatives as Potential Antimicrobial Agents

Microwave Assisted One-Pot Three-Component Synthesis of Novel Pyranocarbazole Derivatives as Antiproliferative Agents and Molecular Docking Studies

Synthesis of novel [1,2,3]triazolo[4′,5′:3,4]pyrrolo[1,2‐a]thieno[2,3‐d] pyrimidines: Potent EGFR targeting anti‐breast cancer agents

Contact Info

Product

Resources

About