Anti-tubercular agents. Part IV: Synthesis and antimycobacterial evaluation of nitroheterocyclic-based 1,2,4-benzothiadiazines

doi:10.1016/j.bmcl.2007.07.027

Bioorganic & Medicinal Chemistry Letters

Volume 17, Issue 19, 1 October 2007, Pages 5419-5422

https://doi.org/10.1016/j.bmcl.2007.07.027 Get rights and content

Abstract

In continuation of our earlier work on benzothiadiazines, we have prepared a series of nitrofuran, nitrothiophene and arylfuran coupled benzothiadiazines and evaluated them for antimycobacterial and antibacterial activities. One of the compounds 2f has shown good in vitro antimycobacterial activity. All the synthesized compounds have shown moderate to good antibacterial activity.

Graphical abstract

Section snippets

Acknowledgment

The authors S.K.A., K.S.R., M.N.A.K. and R.V.C.R.N.C.S. thank CSIR, New Delhi, for the award of research fellowships.

References and notes (26)

B. Murugasu-Oei et al.
J. Antimicrob. Chemother.
(2000)
A. Baliani et al.
J. Med. Chem.
(2005)
M.L. Stewart et al.
Antimicrob. Agents Chemother.
(2004)
G. Aguirre et al.
Eur. J. Med. Chem.
(2004)
N. Bharti et al.
Bioorg. Med. Chem. Lett.
(2002)
H. Cerecetto et al.
Il Farmaco
(1998)
R. Millet et al.
J. Med. Chem.
(2005)
S. Lee et al.
Bioorg. Med. Chem. Lett.
(2007)
S. Lee et al.
J. Med. Chem.
(2005)
P. De Tullio et al.
J. Med. Chem
(2006)
M. Di Bella et al.
Farmaco [Sci.]
(1983)
M. Di Bella et al.
Farmaco [Sci.]
(1979)
A. Kamal et al.
Bioorg. Med. Chem.
(2006)
A.V.N. Reddy et al.
Indian J. Chem.
(1985)

M. Kumar et al.

Diag. Microbiol. Infect. Dis

(2005)

D.E. Snider et al.C. Dye et al.

J. Am. Med. Assoc.

(1999)

A. Pozniak

Ann. N.Y. Acad. Sci.

(2001)

Cited by (31)

Application of multi-walled carbon nanotubes functionalized with hemin to evaluate the electrochemical behavior of nitrofurazone in aqueous media
2023, Electrochimica Acta
A sensor based on a carbon glassy electrode modified with hemin complex and multi-walled carbon nanotubes (MWCNT) was developed as an alternative technique to evaluate the behavior electrochemical of nitrofurazone (NF). This modified electrode showed only one irreversible diffusion-controlled cathodic process in acidic medium, involving four electrons for the hydroxylamine derivative formation with 90 mV potential anticipation and current peak 45 times higher when compared to the bare glassy carbon electrode, GCE. From pH > 9, the NF reduction to hydroxylamine derivative occurred in two steps, being the first one associated to the nitro-anion radical formation in one-electron reversible process. In this case, the reduction potential referring to the radical was anticipated in 250 mV and the peak currents were approximately 13 times higher for sensor modified than those for GCE. The molecular O₂ was confirmed as the best radical scavengers against the glutathione and cysteine and it was 4 times more stable on modified sensor than on the GCE.
Current development of 5-nitrofuran-2-yl derivatives as antitubercular agents
2019, Bioorganic Chemistry
Citation Excerpt :
This will offer the opportunity to study the effects of changes in steric, electronic and hydrophobic properties of substituents on the anti-TB activity of these 5-nitrofuran-based carbothioamides, as well as the introduction of functional groups allowing drug-target interactions that may promote the activity and lessen cytotoxicity. Anti-TB activity profiles of nitrofuran coupled benzothiadiazines 3 and 4 (Fig. 4) were reported by Kamal et al. [35]. Compounds 3a-g (MIC = 1–16 µg/mL) were more potent than compounds 4a-d (MIC = 4–32 µg/mL).
Pulmonary tuberculosis (TB) is an infectious disease caused by Mycobacterium tuberculosis (MTB) and still remains one of the foremost fatal infectious diseases, infecting nearly a third of the worldwide population. The emergencies of multidrug-resistant and extensively drug-resistant tuberculosis (MDR and XDR-TB) prompt the efforts to deliver potent and novel anti-TB drugs. Research aimed at the development of new anti-TB drugs based on nitrofuran scaffold led to the identification of several candidates that were effective against actively growing as well as latent mycobacteria with unique modes of action. This review focuses on the recent advances in nitrofurans that could provide intriguing potential leads in the area of anti-TB drug discovery.
Design, synthesis and in vitro anti-tuberculosis activity of benzo[6,7]cyclohepta[1,2-b]pyridine-1,2,3-triazole derivatives
2017, Bioorganic and Medicinal Chemistry Letters
A series of novel benzo[6,7]cyclohepta[1,2-b]pyridine-1,2,3-triazole hybrids (7a–j & 8a–j) have been designed and synthesized in excellent yields by Huisgen’s [3+2] cyclo addition reaction of 3-(azidomethyl)-2-methyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine (5) with various alkynes 6 in presence of copper sulphate and sodium ascorbate and their structures were confirmed by IR, ¹H NMR, ¹³C NMR and HRMS. The newly synthesized compounds 7a–j & 8a–j were evaluated for their in vitro anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv (ATCC 27294). Among the compounds tested, the compounds 7i and 8g displayed most potent activity with MIC value of 1.56 µg/mL with low cytotoxicity.
Phosphine-mediated addition of 1,2-dicarbonyls to diazenes: An umpolung approach toward N-acyl hydrazone synthesis
2015, Tetrahedron Letters
Using a Kukhtin–Ramirez-like condensation employing hexamethylphosphorous triamide, the addition of 1,2-dicarbonyls to diazenes affords direct access to N-acyl hydrazones in moderate to excellent yields. The strategic assembly of this ubiquitous functional group proceeds through an umpolung disconnect in which an in situ generated acyl anion equivalent reacts with an electrophilic azodicarboxylate to form a new C–N bond. The method presented herein complements traditional condensation approaches toward hydrazone synthesis to access important synthetic intermediates and potentially biologically relevant architectures.
Regioselective synthesis, antimicrobial evaluation and theoretical studies of 2-styryl quinolines
2015, Organic and Biomolecular Chemistry
2-Styryl quinolines (9a–l) have been synthesized regioselectively from 2-methyl-quinoline by using NaOAc in water acetic acid binary solvents and evaluated for their antibacterial activity against both Gram-positive and Gram-negative strains. Among these, the compounds 12 and 8 were found to be active against both bacterial strains. Compounds 9b, 9f, 9g, 9i, 9j and 9k were the most active among the series exhibiting MIC values ranging between 1.9 and 31.2 μg ml⁻¹ against different bacterial strains. Compounds 9j and 9k were found to be as potent as the standard drug ciprofloxacin against Micrococcus luteus, Klebsiella planticola and Staphylococcus aureus. In addition, the compounds showed bactericidal activity; compound 9j was found to be better than ciprofloxacin, with an MBC value of 0.9 μg ml⁻¹ against both M. luteus and K. planticola. The compounds also inhibited biofilm formation, and compound 9j was found to be equipotent to erythromycin against M. luteus and S. aureus MLS16. Further, theoretical studies such as those on druggable properties and PMI plot have been carried out.
1-Oxo-1-fluoro-1,2,4-benzothiadiazines - A new type of cyclic sulfonimidoyl fluorides
2014, Journal of Fluorine Chemistry

View all citing articles on Scopus

View full text

Anti-tubercular agents. Part IV: Synthesis and antimycobacterial evaluation of nitroheterocyclic-based 1,2,4-benzothiadiazines

Abstract

Graphical abstract

Section snippets

Acknowledgment

J. Antimicrob. Chemother.

J. Med. Chem.

Antimicrob. Agents Chemother.

Eur. J. Med. Chem.

Bioorg. Med. Chem. Lett.

Il Farmaco

J. Med. Chem.

Bioorg. Med. Chem. Lett.

J. Med. Chem.

J. Med. Chem

Farmaco [Sci.]

Farmaco [Sci.]

Bioorg. Med. Chem.

Indian J. Chem.

Diag. Microbiol. Infect. Dis

J. Am. Med. Assoc.

Ann. N.Y. Acad. Sci.