- Design, step-economical diversity-oriented synthesis of an N-heterocyclic library containing a pyrimidine moiety: Discovery of novel potential herbicidal agents
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The synthesis of highly diverse libraries has become of paramount importance for obtaining novel leads for drug and agrochemical discovery. Herein, the step-economical diversity-oriented synthesis of a library of various pyrimidine-N-heterocycle hybrids was developed, in which a 4,6-dimethoxypyrimidine core was incorporated into nine kinds of N-heterocycles. A total of 34 structurally diverse compounds were synthesized via a two-step process from very simple and commercially available starting materials. Further, in vivo biological screening of this library identified 11 active compounds that exhibited good post-emergence herbicidal activity against D. sanguinalis at 750 g ai per ha. More importantly, pyrimidine-tetrahydrocarbazole hybrid 5q showed good to excellent herbicidal activity against five test weeds at the same dosage. Pyrimidine-tetrahydrocarbazole hybrids represent a novel class of herbicidal agents that may become promising lead compounds in the herbicidal discovery process.
- Ma, Dong,Yin, Yang,Chen, Ying-Lu,Yan, Yi-Tao,Wu, Jun
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p. 15380 - 15386
(2021/05/19)
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- Convenient synthesis of 1H-benzotriazolylalkylphenols
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(Chemical Equation Presented) A simple, efficient, and environmentally benign method has been developed for the exclusive formation of synthetically significant 1H-benzotriazol-1-ylalkylphenols from hydroxybenzyl alcohols and benzotriazole. Copyright Tayl
- Osyanin, Vitalij A.,Sidorina, Natalia E.,Klimochkin, Yuri N.
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experimental part
p. 2639 - 2647
(2012/07/14)
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- New 5-substituted-1-(2-hydroxybenzoyl)-benzotriazoles, potassium channel activators. IV.
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This paper reports the synthesis of a series of new 5-substituted-1-(2-hydroxybenzoyl)-benzotriazoles, which have been tested for their activity as possible activators of potassium channels. In rat aortic rings, the 'opened' derivatives 1a-f, intermediates of synthesis, showed vasorelaxing properties, with appreciable values of potency. However, the most remarkable effects were recorded for the 2-hydroxybenzoylbenzotriazoles 3a-f, which showed full vasorelaxing efficacy and high potency values. The introduction of a 2-hydroxybenzyl substituent in the 1 position of the benzotriazole ring (compound 7) strongly decreased the activity, showing the importance of the electron-acceptor carbonyl function. The best compound, 3b, was further investigated, in order to evaluate the possible mechanism of action involved in the vasodilator activity. In the vascular model, different potassium channel blockers inhibited the effects of the compound, and an increase of the levels of membrane depolarisation induced a significant reduction of the recorded responses. Compound 3b was also tested in a model of isolated rat heart, retroperfused through the aorta and submitted to a global ischemia/reperfusion cycle. In such an experimental condition, 3b showed an interesting cardioprotective activity. All the above observations are in agreement with the hypothesis of a mechanism linked to the activation of potassium channels.
- Biagi,Giorgi,Livi,Scartoni,Barili,Calderone,Martinotti
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p. 827 - 834
(2007/10/03)
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- o-(α-Benzotriazolylalkyl)phenols: Versatile Intermediates for the Synthesis of Substituted Phenols
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Phenols and naphthols are benzotriazolylmethylated by 1-(hydroxymethyl)-1H-benzotriazole (13) (a formaldehyde derivative) in the o- or (if both o-positions are occupied) in the p-position.The reaction can be extended to other aldehydes in the case of the naphthols.The methylene group in the o-(benzotriazolylmethyl)phenols can be lithiated (but only after trimethylsilyl protection of the hydroxy group) and then substituted by various electrophiles.The benzotriazole residues in both the primary products and in their substituted derivatives can be displaced by the alkylanions of Grignard reagents or by hydride ions allowing the elaboration of many new types of substituted phenols. Key Words: Lithiation/ Mannich reaction/ Alkylation/ Grignard reaction/ Condensation
- Katritzky, Alan R.,Lan, Xiangfu,Lam, Jamshed N.
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p. 1809 - 1817
(2007/10/02)
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