Synthesis, antimicrobial, and mosquito larvicidal activity of 1-aryl-4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5,4-c]quinolin-5-ones

Rajanarendar, E.; Reddy, M. Nagi; Murthy, K. Rama; Reddy, K. Govardhan; Raju, S.; Srinivas, M.; Bhoopathi, Praveen; Rao, M. S. Narasinga

doi:10.1016/j.bmcl.2010.08.060

Cited by 75 publications

(29 citation statements)

References 24 publications

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“…3,4‐Dihydropyrimidin‐2‐(thio)ones 157 containing at position 4 2‐chloro‐ or bromophenyl groups underwent cyclization on heating in ammonia under pressure to give the differently substituted hexahydropyrimido[5,4‐ c ]quinoline 158 in good yields (Scheme ). Similar tricyclic structures have been obtained by using 5‐methylisoxazol‐3‐ylamine as amino component in this reaction .…”

Section: Intramolecular Cycloadditions Of Partially Saturated Pyrimidsupporting

confidence: 71%

Transformations of Di‐ and Tetrahydropyrimidine Derivatives into Condensed Heterocycles with Retention of their Partially Saturated Structure

Remennikov¹

2017

Journal of Heterocyclic Chem

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Section: Intramolecular Cycloadditions Of Partially Saturated Pyrimidsupporting

confidence: 71%

Transformations of Di‐ and Tetrahydropyrimidine Derivatives into Condensed Heterocycles with Retention of their Partially Saturated Structure

Remennikov¹

2017

Journal of Heterocyclic Chem

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“…Compound 76, 77, and 78 were found to be most potent compounds. They exhibit the same antibacterial activity compared to standard drug ciprofloxacin [54]. The structures of potent compounds are shown in Fig.…”

Section: Antibacterial Activitymentioning

confidence: 91%

Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review

Kaur

Chaudhary

Kumar

et al. 2017

European Journal of Medicinal Chemistry

221

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Dihydropyrimidines are the most important heterocyclic ring systems which play an important role in the synthesis of DNA and RNA. Synthetically they were synthesized using Multi-component reactions like Biginelli reaction and Hantzschdihydropyridine. In the past decades, such Biginelli type dihydropyrimidones have received a considerable amount of attention due to the interesting pharmacological properties associated with this heterocyclic scaffold. In this review, we highlight recent developments in this area, with a focus on the DHPMs, recently developed as anti-inflammatory, anti-HIV, anti-tubercular, antifungal anticancer, antibacterial, antifilarial, antihyperglycemic, antihypertensive, analgesic, anti-convulsant, antioxidant, anti-TRPA1, anti-SARS, and anti-cancer activity and α binding affinity.

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“…It suffers from the harsh conditions, long reaction times and also produces low amount of yields, In order to overcome these issues we are developing Cu II ‐Tyr enzyme as a novel eco‐friendly catalyst. Thioxopyrimidine analogs have potent inhibition against mosquito larvae Culex quinquefasciatus . Olfaction plays a major role in organisms and tangled in major activities such as food detection, host‐seeking, reproduction, and also identification of predators .…”

Section: Introductionmentioning

confidence: 99%

Cu^II‐Tyrosinase Enzyme Catalyst‐Mediated Synthesis of 2‐Thioxopyrimidine Derivatives with Potential Mosquito Larvicidal Activity: Spectroscopic and Computational Investigation as well as Molecular Docking Interaction with OBPs of Culex quinquefasciatus

et al. 2020

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A series of 2-thioxo pyrimidine derivatives 1, (1 a-1 e) and 2, (2 a-2 e) were synthesized via Biginelli reaction by using Cu IItyrosinase (Cu II -Tyr) as an enzyme catalyst in up to 80-92% yield. The compounds 1, (1 a-1 e) and 2, (2 a-2 e) were characterized by IR, 1 H NMR, 13 C NMR, mass spectra and elemental analyses. The synthesized compounds 1, (1 a-1 e) and 2, (2 a-2 e) were screened for mosquito larvicidal activity against Culex quinquefasciatus. The compound 2 a was 80% mortality at 100 μg/mL with the LD 50 value of 55.94 μg/mL than the control Permethrin 60.03 μg/mL respectively. Molecular docking studies of synthesized compounds were carried out and the results proposed that the compound 2 a as a potential candidate to mosquito odorant-binding protein 3OGN inhibitors. In addition, computational studies, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies showed that the charge transfer occurs in the inside of the molecule and also gives the chemical reactivity descriptors, and molecular electrostatic potential (MESP) is also calculated. Therefore, experimental and theoretical studies were well supported for the compound 2 a as a potential larvicide activity aganist mosquito larvae of Culex quinquefasciatus.

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Synthesis, antimicrobial, and mosquito larvicidal activity of 1-aryl-4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5,4-c]quinolin-5-ones

Cited by 75 publications

References 24 publications

Transformations of Di‐ and Tetrahydropyrimidine Derivatives into Condensed Heterocycles with Retention of their Partially Saturated Structure

Transformations of Di‐ and Tetrahydropyrimidine Derivatives into Condensed Heterocycles with Retention of their Partially Saturated Structure

Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review

Cu^II‐Tyrosinase Enzyme Catalyst‐Mediated Synthesis of 2‐Thioxopyrimidine Derivatives with Potential Mosquito Larvicidal Activity: Spectroscopic and Computational Investigation as well as Molecular Docking Interaction with OBPs of Culex quinquefasciatus

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Synthesis, antimicrobial, and mosquito larvicidal activity of 1-aryl-4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5,4-c]quinolin-5-ones

Cited by 75 publications

References 24 publications

Transformations of Di‐ and Tetrahydropyrimidine Derivatives into Condensed Heterocycles with Retention of their Partially Saturated Structure

Transformations of Di‐ and Tetrahydropyrimidine Derivatives into Condensed Heterocycles with Retention of their Partially Saturated Structure

Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review

CuII‐Tyrosinase Enzyme Catalyst‐Mediated Synthesis of 2‐Thioxopyrimidine Derivatives with Potential Mosquito Larvicidal Activity: Spectroscopic and Computational Investigation as well as Molecular Docking Interaction with OBPs of Culex quinquefasciatus

Contact Info

Product

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Cu^II‐Tyrosinase Enzyme Catalyst‐Mediated Synthesis of 2‐Thioxopyrimidine Derivatives with Potential Mosquito Larvicidal Activity: Spectroscopic and Computational Investigation as well as Molecular Docking Interaction with OBPs of Culex quinquefasciatus