Potential Insecticidal Activity of Steroidal C-17 Pyrazolinyl Derivatives

Fan, Ning‐Juan; Sang, Wei; Gao, Jin‐Ming; Tang, Jiang‐Jiang

doi:10.5935/0103-5053.20140248

Cited by 5 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To our delight, some compounds displayed more potent insecticidal activity than toosendanin. On the basis of the above furan-modified results and in our endeavor aiming at finding more active natural-product-based insecticidal hits [19,[21][22][23][24], herein, we semi-synthesized C-ring cyclopropyl analogues of fraxinellone by Rh(II)-catalyzed cyclopropanation as insecticidal agents against M. separata.…”

Section: Introductionmentioning

confidence: 99%

Semi-Synthesis of C-Ring Cyclopropyl Analogues of Fraxinellone and Their Insecticidal Activity Against Mythimna separata Walker

et al. 2020

Self Cite

View full text Add to dashboard Cite

Fraxinellone (1) is a naturally occurring degraded limonoid isolated from Meliaceae and Rutaceae plants. As a potential natural-product-based insecticidal agent, fraxinellone has been structurally modified to improve its activity. Furan ring of fraxinellone is critical in exhibiting its insecticidal activity, but with few modifications. Herein, C-ring-modified cyclopropyl analogues were semi-synthesized by Rh(II)-catalyzed cyclopropanation. The structures of the target compounds were well characterized by NMR and HRMS. The precise three-dimensional structural information of 3a was established by X-ray crystallography. Their insecticidal activity was evaluated against Mythimna separata Walker by a leaf-dipping method. Compound 3c exhibited stronger insecticidal activity than 1 and toosendanin against M. separata with teratogenic symptoms during the different periods, implying that cyclopropanation of the furan ring could strengthen the insecticidal activity of fraxinellone.

show abstract

Section: Introductionmentioning

confidence: 99%

Semi-Synthesis of C-Ring Cyclopropyl Analogues of Fraxinellone and Their Insecticidal Activity Against Mythimna separata Walker

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

“…In recent years growing interest has been focused on steroidal 2-pyrazolines and pyrazoles due to their antiandrogenic [18] or direct antiproliferative effect [19,20,21] or their ability to inhibit one of the key regulatory enzymes of steroid biosynthesis [22,23,24,25], which makes them potential candidates for the chemoprevention or treatment of cancerous diseases. Some further derivatives are also known to possess neuroprotective [26], antimicrobial [27] or insecticidal activity [28] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Stereoselective Heterocyclization to Novel Ring d-fused Arylpyrazolines in the Estrone Series

et al. 2019

View full text Add to dashboard Cite

Microwave-assisted syntheses of novel ring d-condensed 2-pyrazolines in the estrone series were efficiently carried out from steroidal α,β-enones and hydrazine derivatives. The ring-closure reaction of 16-benzylidene estrone 3-methyl ether with hydrazine in acetic acid resulted in a 2:1 diastereomeric mixture of two 16,17-cis fused pyrazolines, which is contrary to the former literature data for both stereoselectivity and product structure. However, the cyclization reactions of a mestranol-derived unsaturated ketone with different arylhydrazines in acidic ethanol furnished the heterocyclic products in good to excellent yields independently of the substituents present on the aromatic ring of the reagents applied. The MW conditions also permitted the ring-closure reaction with p-nitrophenylhydrazine which is unfavorable under conventional heating. Moreover, the transformations led to the heterocyclic compounds stereoselectively with a 16α,17α-cis ring junction without being susceptible to spontaneous and promoted oxidation to pyrazoles.

show abstract

“…Recently, we reported the bromination of fraxinellone by N -bromosuccinimide (NBS, as a brominating reagent) and Br 2 (as a catalyst) or by 1,3-dibromo-5,5-dimethylhy-dantoin (DBDMH, another brominating reagent) and following couplings, and found some furan-site modified derivatives displayed more potent insecticidal activity than toosendanin [36]. In our endeavor aiming at finding more active natural product-based insecticidal hits [36, 37, 38, 39, 40], herein we prepared a series of furan-site transformed derivatives of obacunone ( 1 ) by selectively altering furan ring (Fig. 2).…”

Section: Introductionmentioning

confidence: 99%

Furan-site transformations of obacunone as potent insecticidal agents

Xiang

Cao

Dong

et al. 2018

Heliyon

Self Cite

View full text Add to dashboard Cite

Furan ring is a key pharmacophore for insecticidal activity of limoninoids. To develop natural-product-based insecticidal agents, a series of furan-site transformations (2, 3 and 3a–j) of obacunone were synthesized by selective bromination and following coupling reactions without altering other functional groups. Bioassays indicated that derivatives 3e, 3f and 3j displayed more potent insecticidal activity than obacunone and toosendanin against the instar larvae of Mythimna separate Walker. Besides, their structure–activity relationships were discussed.

show abstract

Potential Insecticidal Activity of Steroidal C-17 Pyrazolinyl Derivatives

Cited by 5 publications

References 0 publications

Semi-Synthesis of C-Ring Cyclopropyl Analogues of Fraxinellone and Their Insecticidal Activity Against Mythimna separata Walker

Semi-Synthesis of C-Ring Cyclopropyl Analogues of Fraxinellone and Their Insecticidal Activity Against Mythimna separata Walker

Microwave-Assisted Stereoselective Heterocyclization to Novel Ring d-fused Arylpyrazolines in the Estrone Series

Furan-site transformations of obacunone as potent insecticidal agents

Contact Info

Product

Resources

About