Synthesis of 1-(2-substitutedphenyl-2,3-dihydro-1H-benzo[b][1,4]diazepin-4-yl)naphthalene-2-ol under different solvent conditions as a potent antimicrobial agent

Kottapalle, Gajanan; Shinde, Avinash

doi:10.1016/j.cdc.2021.100690

Cited by 4 publications

(5 citation statements)

References 34 publications

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“…In continuation of earlier research success [35], herein, we wish to report the synthesis of 1,5‐benzothiazepines in different solvent conditions using microwave irradiation. Initially, we attempted cyclocondensation of chalcones 1a (4‐(3‐(2‐hydroxynaphthalen‐1‐yl)‐3)‐oxoprop‐1‐en‐1‐yl) benzonitrile with 2‐aminothiophenol using catalytic amount of piperidine in ethanol as a reaction solvent.…”

Section: Resultsmentioning

confidence: 99%

Microwave‐enhanced heterocyclization: A convenient procedure for 1,5‐benzothiazepine using 2‐ethoxy ethanol solvent and its antibacterial potential

Kottapalle,

Jadhav,

Poul

et al. 2024

Journal of Heterocyclic Chem

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The present research study involves synthesis of 1,5‐benzothiazepines has been prepared, derived from chalcones and 2‐aminothiophenol in a catalytic amount of piperidine using different solvent conditions under microwave irradiation procedure with the aim to test their antibacterial activity and effect of different solvents in the synthesis. It resulted in good yield of 1,5‐benzothiazepines (3a‐j) and proved to be an efficient and environmentally benign procedure. The synthesized compounds were characterized by conventional spectral data and screened for their in vitro antibacterial activity against four pathogenic bacteria using agar diffusion method. The traditional classical heating method takes more reaction time. So, in this study, we have tested microwave irradiation process and found that 2‐ethoxy ethanol as an alternative solvent in reducing the reaction time (up to 4–6 min.) with high yield as compared with classical method. The synthesized compounds 3a, 3c, 3d, 3e, 3 h, 3i, 3j exhibit good to moderate antibacterial activity.

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Section: Resultsmentioning

confidence: 99%

Microwave‐enhanced heterocyclization: A convenient procedure for 1,5‐benzothiazepine using 2‐ethoxy ethanol solvent and its antibacterial potential

Kottapalle,

Jadhav,

Poul

et al. 2024

Journal of Heterocyclic Chem

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“…Naphthol derivatives belong to an important class of chemical compounds found in both synthetic and natural products, exhibiting diverse biological activities [20,21]. Substituted naphthoxyamines have emerged as significant pharmacophores with a wide range of pharmacological and biological properties, including antitumor [22], antimicrobial [23], antibacterial [24], antiproliferative [25], antiparasitic [26], and other activities. Moreover, the search for substances that can modulate the immune status of animals with aseptic inflammation induced by heavy metal salts has been driven by the discovery of the unique properties of piperazine [27] or piperidine [28] propargyl compounds.…”

Section: Resultsmentioning

confidence: 99%

Naphthaleneoxypropargyl-Containing Piperazine as a Regulator of Effector Immune Cell Populations upon an Aseptic Inflammation

Yu,

Sycheva,

Kairanbayeva

et al. 2023

Molecules

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This study investigated the effects of aseptic inflammation and heavy metal exposure on immune responses, as well as the potential immunomodulatory properties of the newly synthesized 1-[1-(2,5-dimethoxyphenyl)-4-(naphthalene-1-yloxy)but-2-ynyl]-4-methylpiperazine complexed with β-cyclodextrin (β-CD). Aseptic inflammation was induced by a subcutaneous injection of turpentine in rats, while heavy metal exposure was achieved through a daily administration of cadmium chloride and lead acetate. The levels of immune cell populations, including cytotoxic T lymphocytes (CTL), monocytes, and granulocytes, were assessed in the spleen. The results showed that aseptic inflammation led to decreased levels of CTL, monocytes, and granulocytes on the 14th day, indicating an inflammatory response accompanied by a migration of effector cells to the inflamed tissues. The exposure to cadmium chloride and lead acetate resulted in systemic immunotoxic effects, with reduced levels of B cells, CD4+ Th cells, monocytes, and granulocytes in the spleen. Notably, piperazine complexed with β-CD (the complex) exhibited significant stimulatory effects on CD4+, CD8+, and myeloid cell populations during aseptic inflammation, even in the presence of heavy metal exposure. These findings suggest the potential immunomodulatory properties of the complex in the context of aseptic inflammation and heavy metal exposure.

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“…Benzodiazepines chalcone derivatives 83 a – h (Figure 14) were reported by Kottapalle and Shinde and evaluated for their antibacterial activity by agar diffusion method [132] . The results found that the compounds ( 83 d and 83 e ) with electron‐withdrawing groups and the compounds ( 83 b , 83 g , and 83 h ) with electron‐releasing groups at the 4‐position on the phenyl rings both demonstrated good antibacterial and antifungal activity.…”

Section: Pharmacological Activitymentioning

confidence: 95%

“…Benzodiazepines chalcone derivatives 83 a-h (Figure 14) were reported by Kottapalle and Shinde and evaluated for their antibacterial activity by agar diffusion method. [132] The results found that the compounds (83 d and 83 e) with electron-withdrawing groups and the compounds (83 b, 83 g, and 83 h) with electron-releasing groups at the 4-position on the phenyl rings both demonstrated good antibacterial and antifungal activity. Compound 83 g exhibits similar antimicrobial action to fluconazole (MIC = 20 μg/mL), with key electron-withdrawing and electron-releasing groups at the para position, suggesting potential for discovering new antibacterial classes.…”

Section: Antibacterialsmentioning

confidence: 96%

Naphthyl‐Based Chalcone Derivatives: A Multifaceted Player in Medicinal Chemistry

Mahesha,

Shetty

2024

ChemistrySelect

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Research has placed a great deal of emphasis on molecule development and discovery with substantial biological profiling in recent years. Despite the significant side effects, medicinal chemists have long strived to synthesize drug molecules with the highest level of therapeutic activity and the lowest possible level of toxicity. The naphthyl‐based chalcone derivatives have drawn attention due to their simple structures and wide range of pharmacological effects. The main focus of this review is to outline the biologically active molecules based on naphthyl moiety‐substituted chalcone derivatives developed over the years. A synopsis of pharmacological screening, including relevant structure‐activity relationships, action mechanisms, and possible therapeutic applications, is provided in this article. It is true that prospective hybrids combining the naphthyl moiety with different chalcone pharmacophores are needed to address drug resistance and improve specificity. Therefore, this review may be useful in the development and design of new, highly successful therapeutic drugs based on previously reported methodologies.

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Synthesis of 1-(2-substitutedphenyl-2,3-dihydro-1H-benzo[b][1,4]diazepin-4-yl)naphthalene-2-ol under different solvent conditions as a potent antimicrobial agent

Cited by 4 publications

References 34 publications

Microwave‐enhanced heterocyclization: A convenient procedure for 1,5‐benzothiazepine using 2‐ethoxy ethanol solvent and its antibacterial potential

Microwave‐enhanced heterocyclization: A convenient procedure for 1,5‐benzothiazepine using 2‐ethoxy ethanol solvent and its antibacterial potential

Naphthaleneoxypropargyl-Containing Piperazine as a Regulator of Effector Immune Cell Populations upon an Aseptic Inflammation

Naphthyl‐Based Chalcone Derivatives: A Multifaceted Player in Medicinal Chemistry

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