Design,synthesis and antifungal activity evaluation of isocryptolepine derivatives |
| |
Affiliation: | 1. Department of Pharmaceutical Chemistry, SANA College of Pharmacy, Kodad, Telangana 508206, India;2. Department of Chemistry, Acharya Nagarjuna University, Nagarjuna Nagar, Andhra Pradesh 522510, India;3. Department of Pharmaceutical Chemistry, G Pulla Reddy College of Pharmacy, Telangana 500028, India;4. Department of Chemistry, Telangana University, Dichpally, Nizamabad, Telangana 503322, India;5. Department of Pharmacy, Vels Institute of Science, Technology and Advanced Studies, Pallavaram, Chennai, Tamil Nadu 600117, India;6. Department of Chemistry, Krishna University, Machilipatnam, Andhra Pradesh 521001, India |
| |
Abstract: | In this paper, the nitrogen atom was inserted into the anthracycline system of the isocryptolepine nucleus to obtain the “Aza”-type structure benzo4,5]imidazo1,2-c] quinazoline. A series of “Aza”-type derivatives were designed, synthesized and evaluated for their antifungal activity against six plant fungi in vitro. Among all derivatives, compounds A-0, B-1 and B-2 showed significant antifungal activity against B. cinerea with the EC50 values of 2.72 μg/mL, 5.90 μg/mL and 4.00 μg/mL, respectively. Compound A-2 had the highest activity against M. oryzae with the EC50 values of 8.81 μg/mL, and compound A-1 demonstrated the most control efficacy against R. solani (EC50, 6.27 μg/mL). Moreover, compound A-0 was selected to investigate the in vivo tests against B. cinerea and the results indicated that the preventative efficacy of it up to 72.80% at 100 μg/mL. Preliminary mechanism studies revealed that after treatment with A-0 at 5 µg/mL, the B. cinerea mycelia appeared curved, collapsed and the cell membrane integrity may be damaged. The reactive oxygen species production, mitochondrial membrane potential and nuclear morphometry of mycelia have been changed, and the membrane function and cell proliferation of mycelia were destroyed. Compounds A-0, A-1, B-1 and B-2 presented weaker toxicities against two cells lines than isocryptolepine. This study lays the foundation for the future development of isocryptolepine derivatives as environmentally friendly and safe agricultural fungicides. |
| |
Keywords: | Isocryptolepine Antifungal activity Structure-activity relationship Mode of action |
本文献已被 ScienceDirect 等数据库收录! |
|