Selective Synthesis of 3‐(α,α‐Dibromoacetyl)‐4‐hydroxy‐6‐methyl‐2<i>H</i>‐pyran‐2‐one as an Excellent Precursor for the Synthesis of 2‐Substituted 4‐(4‐Hydroxy‐6‐methyl‐2<i>H</i>‐2‐oxopyran‐3‐yl)thiazoles as Antimicrobial and Antifungal Agents

Kapoor, Jitander K.; Prakash, Richa; Kumar, Ajay; Saini, Deepika; Arora, Loveena

doi:10.1002/jhet.3116

Cited by 6 publications

(3 citation statements)

References 45 publications

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“…Kapoor et al synthesized some DHA‐based thiazoles, and screened them for their in vitro antimicrobial activities. [ 55 ] The results of the study revealed that compound 27 was found to be the most potent against all the tested microbes with pMIC value of 2.043 µmol/mL against B. subtilis and C. albicans , which is comparable to ofloxacin (pMIC = 3.080) and fluconazole (pMIC = 3.008). SAR studies demonstrated that the high activity of compound 27 is due to the presence of electron‐withdrawing ‐NO 2 group.…”

Section: Biological Activities Of Dha‐based Compoundsmentioning

confidence: 99%

Dehydroacetic acid a privileged medicinal scaffold: A concise review

Grover,

Kumar,

Tittal

et al. 2023

Archiv der Pharmazie

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From the last decade, research on dehydroacetic acid (DHA) and its derivatives has increased immensely due to its significant role in various fields, including medicine, cosmetics, food industry, and so on. In the medicinal area, DHA plays an essential role in developing novel action‐based drugs, which are helpful for treating various diseases. Besides its plethora of biological applications, its chelating ability offers the easiest synthetic route for synthesizing more active metal complexes. DHA derivatives along with their metal complexes show a number of biological activities and also exhibit various interactions with multiple biological targets. This article summarizes recent medicinal applications (2000‐onwards) of DHA‐based compounds and their analogs, along with their structure–activity relationship (SAR) analysis. Their interactions with different target enzymes are also discussed. This information derived from SAR analysis would be helpful for medicinal chemists working on the development of drugs based on heterocyclic frameworks, particularly those based on the DHA scaffold.

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Section: Biological Activities Of Dha‐based Compoundsmentioning

confidence: 99%

Dehydroacetic acid a privileged medicinal scaffold: A concise review

Grover,

Kumar,

Tittal

et al. 2023

Archiv der Pharmazie

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“…Also, it was more potent than Fluconazole against both C. albicans (MIC 1.582 µg/mL), and Aspergillus niger (MIC 1.281 µg/mL). 78 against Bacillis subtilis (MIC 1.95 µg/mL). And showed superior activity than Amphotericin B against Syncephalastrum racemosum (MIC 0.49 µg/mL) (Scheme 35).…”

Section: Figure 36 2-(2-allylidenehydrazinyl)thiazole 130mentioning

confidence: 99%

Synthetic Approaches toward Certain Structurally Related Antimicrobial Thiazole Derivatives (2010-2020)

Abuo‐Rahma¹,

Hassan²,

Hassan³

et al. 2021

HETEROCYCLES

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In the present literature review, we comprehensively discuss different methods of synthesis of published antimicrobial thiazole derivatives in the last decade mainly those which showed antibacterial, antimycobacterial and/or antifungal activity. Owing to the great diversity of thiazole-derived antimicrobial agents, we organized most of them chemically in stipulated classes. In each class, we mentioned common methods of thiazole ring closure and indicated antimicrobial activity of the most active derivatives in clear and simple way. CONTENTS1.

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“…In 2018, Arora and his co‐workers, synthesized various bioactive thiazole derivatives 227 from 3‐(α,α‐ dibromoacetyl)‐4‐hydroxy‐6‐methyl‐2 H ‐pyran‐2‐one 228 by using various thiourea derivatives 229 in alcoholic solvent (Scheme B). Most of the synthesized compounds were found to exhibit potent antibacterial and antifungal activity.…”

Section: The Gem‐dihaloketones In the Synthesis Of Heterocyclic Framementioning

confidence: 99%

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

Sadhukhan

Santhi

Baire

2020

Chemistry A European J

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The α,α‐dihalocarbonyl moiety is a bifunctional system with a gem‐dihalocarbon and a carbonyl carbon in 1,2‐fashion. This is one of the privileged scaffolds in medicinal chemistry due to its chemical and metabolic stability and lipophilicity. They have also been found in numerous structurally divergent natural products and most of their fabricated structures have already been in medicinal use. Apart from their important use in medicinal chemistry, the α,α‐dihalocarbonyl groups have been employed as key building blocks for the development of novel synthetic strategies and utilized as intermediates in total synthesis. In addition to the traditional transformations such as oxidations, reductions, and C−C bond formations, recently several new and non‐classical reactions have also been developed. This review provides short description of existing methods for their synthesis and detailed discussion on the efforts for the discovery and development of new reactions by employing α,α‐dihaloketones as synthetic building blocks. We have presented their use as key functional groups for the synthesis of polycyclic systems of medicinal and material importance and natural products.

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Selective Synthesis of 3‐(α,α‐Dibromoacetyl)‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one as an Excellent Precursor for the Synthesis of 2‐Substituted 4‐(4‐Hydroxy‐6‐methyl‐2H‐2‐oxopyran‐3‐yl)thiazoles as Antimicrobial and Antifungal Agents

Cited by 6 publications

References 45 publications

Dehydroacetic acid a privileged medicinal scaffold: A concise review

Dehydroacetic acid a privileged medicinal scaffold: A concise review

Synthetic Approaches toward Certain Structurally Related Antimicrobial Thiazole Derivatives (2010-2020)

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

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