Esraa Khamies, Etify A. Bakhite, Talaat I. El-Emary, Mohamed A. Gad, Shams H. Abdel-Hafez, Aly Abdou, Awad I. Said
{"title":"作为杀虫剂的吡啶衍生物:第 6 部分。3-(取代)甲硫基-5,6,7,8-四氢异喹啉-4-甲腈的设计、合成、分子对接和对蚜虫(Glover,1887 年)的杀虫活性","authors":"Esraa Khamies, Etify A. Bakhite, Talaat I. El-Emary, Mohamed A. Gad, Shams H. Abdel-Hafez, Aly Abdou, Awad I. Said","doi":"10.1021/acs.jafc.4c03947","DOIUrl":null,"url":null,"abstract":"Three new series of 3-(substituted)methylthio-4-cyano-5,6,7,8-tetrahydroisoquinolines were designed and synthesized starting from readily available materials, 7-acetyl-4-cyano-1,6-dimethyl-6-hydroxy-8-(4-pyridyl, 3-pyridyl, phenyl, 4-methoxyphenyl, or 4-chlorophenyl)-5,6,7,8-tetrahydrosoquinoline-3(2<i>H</i>)-thiones <b>2a</b>–<b>e</b> in high yields and very pure states. Thus, compounds <b>2a</b>–<b>e</b> were reacted with some chloro reagents, namely, <i>N</i>-aryl-2-chloroacetamides <b>3a</b>–<b>f</b> and <i>N</i>-(naphthalen-2-yl)-2-chloroacetamide (<b>3g</b>) under mild basic conditions to give the first two series of the target compounds, 3-(<i>N</i>-aryl)carbamoylmethylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles <b>4a</b>–<b>l</b> and <b>5a</b>–<b>e</b>, respectively. Reaction of compounds <b>2d</b>,<b>e</b> with ethyl chloroacetate under the same conditions gave the other series, 3-ethoxycarbonyl-methylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles <b>6d</b>,<b>e</b>. Structural formulas of all of the new compounds were elucidated and confirmed by elemental and spectral analyses. The insecticidal activity of all synthesized 5,6,7,8-tetrahydrosoquinolines toward the nymphs and adults of <i>Aphis gossypii</i> were screened. The results revealed the promising insecticidal activity of some tested compounds. Moreover, the structure–activity relationships as well as molecular docking of some representative compounds were evaluated.","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7000,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Pyridine Derivatives as Insecticides: Part 6. Design, Synthesis, Molecular Docking, and Insecticidal Activity of 3-(Substituted)methylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles Toward Aphis gossypii (Glover, 1887)\",\"authors\":\"Esraa Khamies, Etify A. Bakhite, Talaat I. El-Emary, Mohamed A. Gad, Shams H. Abdel-Hafez, Aly Abdou, Awad I. Said\",\"doi\":\"10.1021/acs.jafc.4c03947\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Three new series of 3-(substituted)methylthio-4-cyano-5,6,7,8-tetrahydroisoquinolines were designed and synthesized starting from readily available materials, 7-acetyl-4-cyano-1,6-dimethyl-6-hydroxy-8-(4-pyridyl, 3-pyridyl, phenyl, 4-methoxyphenyl, or 4-chlorophenyl)-5,6,7,8-tetrahydrosoquinoline-3(2<i>H</i>)-thiones <b>2a</b>–<b>e</b> in high yields and very pure states. Thus, compounds <b>2a</b>–<b>e</b> were reacted with some chloro reagents, namely, <i>N</i>-aryl-2-chloroacetamides <b>3a</b>–<b>f</b> and <i>N</i>-(naphthalen-2-yl)-2-chloroacetamide (<b>3g</b>) under mild basic conditions to give the first two series of the target compounds, 3-(<i>N</i>-aryl)carbamoylmethylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles <b>4a</b>–<b>l</b> and <b>5a</b>–<b>e</b>, respectively. Reaction of compounds <b>2d</b>,<b>e</b> with ethyl chloroacetate under the same conditions gave the other series, 3-ethoxycarbonyl-methylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles <b>6d</b>,<b>e</b>. Structural formulas of all of the new compounds were elucidated and confirmed by elemental and spectral analyses. The insecticidal activity of all synthesized 5,6,7,8-tetrahydrosoquinolines toward the nymphs and adults of <i>Aphis gossypii</i> were screened. The results revealed the promising insecticidal activity of some tested compounds. 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Pyridine Derivatives as Insecticides: Part 6. Design, Synthesis, Molecular Docking, and Insecticidal Activity of 3-(Substituted)methylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles Toward Aphis gossypii (Glover, 1887)
Three new series of 3-(substituted)methylthio-4-cyano-5,6,7,8-tetrahydroisoquinolines were designed and synthesized starting from readily available materials, 7-acetyl-4-cyano-1,6-dimethyl-6-hydroxy-8-(4-pyridyl, 3-pyridyl, phenyl, 4-methoxyphenyl, or 4-chlorophenyl)-5,6,7,8-tetrahydrosoquinoline-3(2H)-thiones 2a–e in high yields and very pure states. Thus, compounds 2a–e were reacted with some chloro reagents, namely, N-aryl-2-chloroacetamides 3a–f and N-(naphthalen-2-yl)-2-chloroacetamide (3g) under mild basic conditions to give the first two series of the target compounds, 3-(N-aryl)carbamoylmethylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles 4a–l and 5a–e, respectively. Reaction of compounds 2d,e with ethyl chloroacetate under the same conditions gave the other series, 3-ethoxycarbonyl-methylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles 6d,e. Structural formulas of all of the new compounds were elucidated and confirmed by elemental and spectral analyses. The insecticidal activity of all synthesized 5,6,7,8-tetrahydrosoquinolines toward the nymphs and adults of Aphis gossypii were screened. The results revealed the promising insecticidal activity of some tested compounds. Moreover, the structure–activity relationships as well as molecular docking of some representative compounds were evaluated.
期刊介绍:
The Journal of Agricultural and Food Chemistry publishes high-quality, cutting edge original research representing complete studies and research advances dealing with the chemistry and biochemistry of agriculture and food. The Journal also encourages papers with chemistry and/or biochemistry as a major component combined with biological/sensory/nutritional/toxicological evaluation related to agriculture and/or food.