Synthesis and Analgesic, Anthelmintic, and Insecticidal Activity of 3,3-Dialkyl-1-(2-Phenylamino-2-Thioxoethyl)-3,4-Dihydroisoquinolinium Chlorides

Михайловский, А. Г.; Yusov, A. S.; Makhmudov, R. R.; Старкова, А. В.; Рудакова, И. П.

doi:10.1007/s11094-018-1887-1

Cited by 10 publications

(3 citation statements)

References 14 publications

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“…The dihedral angle between the mean planes of the C11•••C16 and C1/C2/ C7/C8/C9/N1 rings is 79.20(3)°. A puckering analysis 31 of the C2•••C7 ring yielded the parameters Q = 0.5206(11) Å, θ = 130.09 (12)°and φ= 339.36 (15).°Its conformation can be described as a slightly twisted envelope with C5 being the point of the flap. S3) form inversion dimers which are linked into layers parallel to (101̅ ) by C6−H6A•••O3 and C16− H16•••O3 hydrogen bonds (Table S3 and Figure S1).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Isoquinolines and partially hydrogenated derivatives are important classes of heterocyclic compounds; their syntheses, reactions, and applications have been reviewed. − In general, many isoquinoline derivatives are reported to be antihypertensive, antioxidant, anti-inflammatory, , antipyretic, analgesic, antimicrobial, and antimalarial, as well as antidepressants and antipsychotic agents, antitumor or antiproliferative, − and insecticidal. ,− From a chemistry point of view, 5,6,7,8-tetrahydroisoquinolines and 7,8-dihydroisoquinolines are more closely related to the pyridine scaffold than that to the isoquinoline one. In other words, the pyridine ring, the main heterocyclic constituent of 5,6,7,8-tetrahydroisoquinolines and 7,8-dihydroisoquinolines, is the framework of many neonicotinoid insecticides …”

Section: Introductionmentioning

confidence: 99%

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Pyridine Derivatives as Insecticides. Part 3. Synthesis, Crystal Structure, and Toxicological Evaluation of Some New Partially Hydrogenated Isoquinolines against Aphis gossypii (Glover, 1887)

Bakhite

Marae

Gad

et al. 2022

J. Agric. Food Chem.

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Three new series of isoquinolines, that is, 7-acetyl-3-acetonylsulfanyl-8-aryl-1,6-dimethyl-6-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles (3a–c); 3-acetonylsulfanyl-8-aryl-1,6-dimethyl-7,8-dihydroisoquinoline-4-carbonitriles (4a–c); and 7-acetyl-8-aryl-1,6-dimethyl-3-ethylsulfanyl-7,8-dihydroisoquinoline-4-carbo-nitriles (6a,b) were carefully synthesized. Also, pyrazoloisoquinoline 7 was used as a precursor for synthesis of 7-ethylsulfanyl-4-phenyl-1-thiocarbamoyl-3,5,9a-trimethyl-3a,4,9,9a-tetrahydro-1H-pyrazolo[3,4-g]isoquinoline-8-carbonitrile (8); 7-benzyl-sulfanyl-4-phenyl-1-thiocarbamoyl-3,5,9a-trimethyl-3a,4,9,9a-tetrahydro-1H-pyrazolo[3,4-g]isoquinoline-8-carbonitrile (9); and 7-ethylsulfanyl-1-(4-oxo-4,5-dihydrothiazol-2-yl)-4-phenyl-3,5,9a-trimethyl-3a,4,9,9a-tetrahydro-1H-pyrazolo[3,4-g]isoquinoline-8-carbonitrile (10). Moreover, the crystal structures of two representative compounds were determined. Eleven new compounds 3a, 4a, 3b, 4b, 3c, 4c, 6a, 6b, 8, 9, and 10 were screneed for their toxicological activity against nymphs and adults of Aphis gossypii by using acetamprid, as a reference. After 24 h of treatment, the bioefficacy results indicate that all tested isoquinolines exhibit toxicological activity that varied from very high to low against nymphs and adults of Aphis gossypii, some compounds showing activity near to that of acetampirid and only one compound which possesses higher activity against nymphs and adults of Aphis gossypii than that of acetampirid itself.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Pyridine Derivatives as Insecticides. Part 3. Synthesis, Crystal Structure, and Toxicological Evaluation of Some New Partially Hydrogenated Isoquinolines against Aphis gossypii (Glover, 1887)

Bakhite

Marae

Gad

et al. 2022

J. Agric. Food Chem.

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“…Many thioamide compounds are beneficial, especially with biological activities, such as antimicrobial, anticancer, antituberculosis, and anthelmintic properties [ 32 , 33 , 34 , 35 , 36 ]. DFPM, which belongs to the thioamide class, exhibits diverse activities, including inhibiting ABA signaling and primary root meristem activity by activating plant immune signaling.…”

Section: Discussionmentioning

confidence: 99%

Novel Compounds Derived from DFPM Induce Root Growth Arrest through the Specific VICTR Alleles of Arabidopsis Accessions

Kim,

Cho,

Kim

2023

Life

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The small compound [5-(3,4-dichlorophenyl) furan-2-yl]-piperidine-1-ylmethanethione (DFPM) inhibits ABA responses by activating effector-triggered immune signal transduction in Arabidopsis. In addition to the known function of DFPM as an antagonist of ABA signaling, DFPM causes accession-specific root growth arrest in Arabidopsis Columbia-0 via the TIR-NLR protein VICTR (VARIATION IN COMPOUND TRIGGERED ROOT growth response) in an EDS1/PAD4/RAR1/SGT1B-dependent manner. Although DFPM could control the specific steps of various cellular responses, the functional residues for the activity of DFPM or the existence of a stronger version of DFPM modification have not been characterized thoroughly. This study analyzed twenty-two DFPM derivatives during root growth arrest, inhibition of ABA signaling, and induction of biotic signal transduction to determine critical residues that confer the specific activity of DFPM. Furthermore, this study identified two more Arabidopsis accessions that generate significant root growth arrest in response to DFPM derivatives dependent on multiple amino acid polymorphisms in the coding region of VICTR. The isolation of novel compounds, such as DFPM-5, and specific amino acid polymorphisms critical for the compound-induced responses will help determine the detailed regulatory mechanism for how DFPM regulates abiotic and biotic stress signaling interactions.

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Rhodium‐Catalysed [4+2] Annulation of Aromatic Oximes with Terminal Alkenes by C−H/N−O Functionalization towards 3,4‐Dihydroisoquinolines

Zhang

Ouyang

et al. 2019

Adv Synth Catal

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Rhodium (Rh)-catalysed [4 + 2] annulation of aromatic oximes with common terminal alkenes for the synthesis of 3,4-dihydroisoquinolines is presented. Through the cooperation of a Rh (III) catalyst and a catalytic amount of K 2 HPO 4 base, the reaction enables the formation of two new bonds, a C(sp 2 )À C(sp 3 ) bond and a C(sp 3 )À N bond, in a single reaction via functionalization of both the CÀ H and NÀ O bonds and provides a practical method to produce 3,4-dihydroisoquinolines with exquisite selectivity and excellent compatibility of functional groups.

show abstract

Synthesis and Analgesic, Anthelmintic, and Insecticidal Activity of 3,3-Dialkyl-1-(2-Phenylamino-2-Thioxoethyl)-3,4-Dihydroisoquinolinium Chlorides

Cited by 10 publications

References 14 publications

Pyridine Derivatives as Insecticides. Part 3. Synthesis, Crystal Structure, and Toxicological Evaluation of Some New Partially Hydrogenated Isoquinolines against Aphis gossypii (Glover, 1887)

Pyridine Derivatives as Insecticides. Part 3. Synthesis, Crystal Structure, and Toxicological Evaluation of Some New Partially Hydrogenated Isoquinolines against Aphis gossypii (Glover, 1887)

Novel Compounds Derived from DFPM Induce Root Growth Arrest through the Specific VICTR Alleles of Arabidopsis Accessions

Rhodium‐Catalysed [4+2] Annulation of Aromatic Oximes with Terminal Alkenes by C−H/N−O Functionalization towards 3,4‐Dihydroisoquinolines

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