Pyrazolo[3,4-b]pyridin-3(2H)-one derivatives: Synthesis and their investigation of mosquito larvicidal activity

被引:13
作者
Al-Zharani, Mohammed [1 ]
Al-Eissa, Mohammed S. [1 ]
Rudayni, Hassan A. [1 ]
Ali, Daoud [2 ]
Alkahtani, Saad [2 ]
Surendrakumar, Radhakrishnan [3 ]
Idhayadhulla, Akbar [3 ]
机构
[1] Imam Mohammad Ibn Saud Islamic Univ, Coll Sci, Biol Dept, Riyadh 11623, Saudi Arabia
[2] King Saud Univ, Coll Sci, Dept Zool, Riyadh 11461, Saudi Arabia
[3] Bharathidasan Univ, Res Dept Chem, Nehru Mem Coll, Puthanampatti 621007, Tamil Nadu, India
关键词
Hydrazine; Pyrazolo[3; b ]pyridin; Environmental toxicity; Larvicidal activity; BOTANICAL INSECTICIDES; NATURAL-PRODUCTS; NOSTOCINE-A; HYDRAZINE; DISCOVERY; POTENT;
D O I
10.1016/j.jksus.2021.101767
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
In this study, nitrogen-nitrogen bonds containing compounds such as hydrazine derivatives are examined. There are relatively few hydrazine molecules in nature, but some have been isolated from plants, marine organisms and microorganisms. Thus, hydrazine molecules are widely used in the manufacture of synthetic catalysts, agriculture chemicals, pesticides, and also cause irreversible pollution to air, water, and soil. Hydrazine compounds were evaluated via larvicidal profile in a stagnant water system. According to the above observation, new 1H-pyrazolo[3,4-b]pyridin-3(2H)-one derivatives can be synthesized via catalyst free green chemistry approach. A range of FT-IR spectroscopic measures, 1H and 13C NMR, as well as mass spectra, were used to characterize the compounds (2a-e). The compound 2e was more potent (95,6% mortality, LD50: 20.1 mg/ mL) against Culex quinquefasciatus than natural pyrazolidine derivatives. Therefore, the objective of this study, prospered with a few of the pyrzolopyridine hydrazine models, which are demonstrated to be low toxic environmentally safe and high potential larvicidal profile. (c) 2021 The Authors. Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
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页数:7
相关论文
共 41 条
[31]   Possible allelopathic effects of cyanotoxins, with reference to microcystin-LR, in aquatic ecosystems [J].
Pflugmacher, S .
ENVIRONMENTAL TOXICOLOGY, 2002, 17 (04) :407-413
[32]   Amperometric and voltammetric detection of hydrazine using glassy carbon electrodes modified with carbon nanotubes and catechol derivatives [J].
Salimi, Abdollah ;
Miranzadeh, Layla ;
Hallaj, Rahman .
TALANTA, 2008, 75 (01) :147-156
[33]   WITHASOMNINE . A PYRAZOLE ALKALOID FROM WITHANIA SOMNIFERA DUN [J].
SCHROTER, HB ;
NEUMANN, D ;
KATRITZKY, AR ;
SWINBOUR.FJ .
TETRAHEDRON, 1966, 22 (08) :2895-+
[34]   Botanical insecticides for controlling agricultural pests:: Piperamides and the Colorado potato beetle Leptinotarsa decemlineata say (Coleoptera: Chrysomelidae) [J].
Scott, IM ;
Jensen, H ;
Scott, JG ;
Isman, MB ;
Arnason, JT ;
Philogène, BJR .
ARCHIVES OF INSECT BIOCHEMISTRY AND PHYSIOLOGY, 2003, 54 (04) :212-225
[35]   HYDRAZINE DEGRADATION IN AQUATIC SYSTEMS [J].
SLONIM, AR ;
GISCLARD, JB .
BULLETIN OF ENVIRONMENTAL CONTAMINATION AND TOXICOLOGY, 1976, 16 (03) :301-309
[36]   Metabolites of orally active NO-independent pyrazolopyridine stimulators of soluble guanylate cyclase [J].
Straub, A ;
Benet-Buckholz, J ;
Fröde, R ;
Kern, A ;
Kohlsdorfer, C ;
Schmitt, P ;
Schwarz, T ;
Siefert, HM ;
Stasch, JP .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (06) :1711-1717
[37]   Discovery of 3-{5-[(6-Amino-1H-pyrazolo[3,4-b]pyridine-3-yl)methoxy]-2-chlorophenoxy}-5-chlorobenzonitrile (MK-4965): A Potent, Orally Bioavailable HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitor with Improved Potency against Key Mutant Viruses [J].
Tucker, Thomas J. ;
Sisko, John T. ;
Tynebor, Robert M. ;
Williams, Theresa M. ;
Felock, Peter J. ;
Flynn, Jessica A. ;
Lai, Ming-Tain ;
Liang, Yuexia ;
McGaughey, Georgia ;
Liu, Meiquing ;
Miller, Mike ;
Moyer, Gregory ;
Munshi, Vandna ;
Perlow-Poehnelt, Rebecca ;
Prasad, Sridhar ;
Reid, John C. ;
Sanchez, Rosa ;
Torrent, Maricel ;
Vacca, Joseph P. ;
Wan, Bang-Lin ;
Yan, Youwei .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (20) :6503-6511
[38]   Constituents of Volatile Compounds Derived from Melaleuca alternifolia Leaf Oil and Acaricidal Toxicities against House Dust Mites [J].
Yang, Ji-Yeon ;
Cho, Kyoung-Shik ;
Chung, Nam-Hyun ;
Kim, Chung-Ho ;
Suh, Joo-Won ;
Lee, Hoi-Seon .
JOURNAL OF THE KOREAN SOCIETY FOR APPLIED BIOLOGICAL CHEMISTRY, 2013, 56 (01) :91-94
[39]   Adulticidal activity of five essential oils against Culex pipiens quinquefasciatus [J].
Yang, P ;
Ma, YJ ;
Zheng, SQ .
JOURNAL OF PESTICIDE SCIENCE, 2005, 30 (02) :84-89
[40]   A piperidine amide extracted from Piper longum L. fruit shows activity against Aedes aegypti mosquito larvae [J].
Yang, YC ;
Lee, SG ;
Lee, HK ;
Kim, MK ;
Lee, SH ;
Lee, HS .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (13) :3765-3767