Synthesis, utility and medicinal importance of 1,2- &amp; 1,4-dihydropyridines

Sharma, Vivek; Singh, Sunil Kumar

doi:10.1039/c6ra24823c

Cited by 143 publications

(76 citation statements)

References 152 publications

(87 reference statements)

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“…Dihydroquinolines (DHQs) and their fused analogues are heterocyclic scaffolds that are ubiquitous in natural products, therapeutics, fluorophores and dyes [179]. They are structures of great versatility, and their physical and chemical properties can be finely tuned using synthetic chemistry [180].…”

Section: Fused Dihydroquinoline-based Anticancer Heterocyclic Systemsmentioning

confidence: 99%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review.Molecules 2020, 25, 505 2 of 71 acetylcholinesterase inhibitors, anti-HIV, antimicrobial, antioxidant, anti-mycobacterial and anticancer activities ( Figure 1). It is noteworthy that 64% and 16% of the supporting literature found for this review correspond to heterocyclic structures with anticancer and antimicrobial activities, respectively. Scheme 2. Three-component synthesis of 3,4-dihydropyrimidinones/thiones type 7 under microwave irradiation, for anti-inflammatory activity.Patil et al., reported a one-pot pseudo-five-component synthesis of highly functionalized tetrahydropyridines 9 using Cu(OTf) 2 as catalyst, Scheme 3. In vitro anti-inflammatory activity of the obtained compounds 9 was determined against matrix metalloproteinases (MMPs) as MMP-2 and MMP-9 by using gelatin zymography [29]. Scheme 3. Multicomponent Cu(OTf) 2 catalyzed synthesis of substituted tetrahydropyridines 9 for anti-inflammatory activity.A highly diastereoselective synthesis (exclusively the cis isomer is formed), of chromeno β-lactam hybrids 13/14 was also achieved by an efficient one-pot three-component reaction between either 5,5-dimethylcyclohexane-1,3-dione (10a) or 4-hydroxycoumarin (10b), diverse benzaldehydes 11 and malononitrile (12), in the presence of DABCO under reflux conditions (Scheme 4). Scheme 4. Three-component synthesis of β-lactam hybrids 13/14 for anti-inflammatory activity.The synthesized compounds (13 in 80-95% yield) and (14 in 82-95% yield) were screened for anti-inflammatory activity (as well as for anticancer activity, please see Section 3.13.13. Compound 13b (Ar = 4-ClC 6 H 4 , Ar 1 = 4-MeC 6 H 4 ) was the most active of all the chromeno β-lactam hybrids 13/14 tested, with a 19.8 anti-inflammatory ratio, although, it resulted less active than the reference drug dexamethasone corticosteroid used for the treatment of rheumatoid and skin inflammation [30].

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Section: Fused Dihydroquinoline-based Anticancer Heterocyclic Systemsmentioning

confidence: 99%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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“…Several past reviews provide a complete survey on the synthetic methodologies for realizing the Hantzsch reaction, as well as on the libraries of the resulting structurally different 1,4-DHPs. [40][41][42] The mechanism of the Hantzsch reaction is one of the most complex among all MCRs.…”

Section: The Hanztsch Reactionmentioning

confidence: 99%

Similarity and Competition between Biginelli and Hantzsch Reactions: an Opportunity for Modern Medicinal Chemistry

2020

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Similarity and competition between multicomponent reactions with similar mechanisms and leading to similar scaffolds can be a useful tool for medicinal chemistry. In this review, we have summarized the studies disclosing the mechanism of such competition between the Biginelli and Hantzsch reactions. We focused our attention in particular on those studies exploiting similarity and competition as an opportunity to switch from one reaction to another, by simply changing the reaction conditions, thus opening the possibility to obtain, using the same experimental setup, molecular libraries of both 3,4‐dihydropyrimidin‐2‐(1H)‐ones (DHPM) and 1,4‐dihydropyridines (1,4‐DHP) scaffolds. The aim of this review is to encourage further exploitation of such synthetic strategy as a tool for enhancing the chemical space in medicinal chemistry.

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“…1) are the unsymmetrical Hantzsch derivatives of 1,4-DHPs obtained via a fourcomponent process (4CR), and many methodologies have been reported for their synthesis. [7][8][9] In recent years, much consideration has been given to the synthesis of the PHQ derivatives because of their pharmacological signicance, which makes them potential targets for a number of biological applications. [10][11][12][13] However, the important results around these small biologically active molecules have inspired further research to identify new, similar substances with diverse structures and to better understand the relationship between the variation in the chemical structure and biological activity.…”

Section: Introductionmentioning

confidence: 99%