Indoloquinoline Alkaloids as Antimalarials: Advances, Challenges, and Opportunities DOI Creative Commons
Prakash T. Parvatkar,

Khaly Diagne,

Yingzhao Zhao

et al.

ChemMedChem, Journal Year: 2024, Volume and Issue: unknown

Published: June 6, 2024

Abstract Malaria infections affect almost half of the world‘s population, with over 200 million cases reported annually. Cryptolepis sanguinolenta , a plant native to West Africa, has long been used across various regions Africa for malaria treatment. Chemical analysis revealed that is abundant in indoloquinolines, which have shown possess antimalarial properties. Cryptolepine, neocryptolepine, and isocryptolepine are well‐studied indoloquinoline alkaloids known their potent activity. However, structural rigidity associated cellular toxicity major drawbacks preclinical development. This review focuses on potential (cryptolepine, isocryptolepine) as scaffolds drug discovery. The article delves into effects vitro vivo, well proposed mechanisms action structure‐activity relationship studies. Several studies aim improve these leads by reducing cytotoxicity while preserving or enhancing activity gaining insights action. These investigations highlight indoloquinolines scaffold developing new drugs.

Language: Английский

Recent Advances in the Synthesis of Fused‐Cyclic Quinolines DOI

Shahab A. Darbandizadeh,

Saeed Balalaie

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(5)

Published: Feb. 16, 2024

Abstract Fused quinolines have gained substantial attention due to their significant biological and wide‐spectrum synthetic applications. This review supplies an encyclopedic document regarding the approaches developed for synthesis of fused‐cyclic based on ring volume size reported thus far. collected information will be valuable medicinal chemists obtain knowledge designing new in order access active compounds.

Language: Английский

Citations

6
Regiodivergent Synthesis and Biological Activities of Indoloquinoline Based Compounds DOI Creative Commons

Katja S. Håheim,

Magne O. Sydnes

The Chemical Record, Journal Year: 2024, Volume and Issue: 24(3)

Published: Feb. 6, 2024

Abstract Cryptolepine, neocryptolepine, and isocryptolepine have remained popular synthetic targets ever since their isolation from the aqueous extracts of West African climbing shrub Cryptolepis sanguinolenta . These natural alkaloids were found to contain significant antimalarial, antiproliferative antimicrobial activities, making them ideal starting points for development novel drug candidates. As product synthesis is often plagued with step‐heavy procedures poor atom economy, discovery protocols addressing these concerns are sorely needed. In our laboratories, we devoted efforts into regiodivergent whereby two indoloquinoline products, namely neocryptolepine 11 H ‐indolo[3,2‐ c ]quinolines, could be assembled in only a few steps common readily available material. Our endeavors meet goals include cascade palladium‐catalyzed Suzuki‐Miyuara cross‐coupling intramolecular C−N bond formation photochemical nitrene insertion strategy. Furthermore, methods also allowed construction several diversely functionalized derivatives which subjected biological evaluations.

Language: Английский

Citations

3
Regiodivergent Synthesis of 11H‐Indolo[3,2‐c]quinolines and Neocryptolepine from a Common Starting Material DOI Creative Commons

Katja S. Håheim,

Bjarte Aarmo Lund, Magne O. Sydnes

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(13)

Published: Feb. 23, 2023

Abstract A large number of diversely functionalized analogs the bioactive natural products neocryptolepine and isocryptolepine have been prepared from a series 3‐bromoquinoline derivatives. The neocryptolepines were obtained by Pd 0 ‐catalyzed C−C bond coupling followed C−N formation in yields up to 80 %, whereas indoloquinolines Suzuki‐Miyaura cross‐coupling azidation‐photochemical cyclization ranging traces 95 % yield.

Language: Английский

Citations

6
Harnessing the power of natural alkaloids: the emergent role in epilepsy therapy DOI Creative Commons
Siyu Li, Xinyu Lin,

Lijuan Duan

et al.

Frontiers in Pharmacology, Journal Year: 2024, Volume and Issue: 15

Published: June 19, 2024

Graphical Abstract Therapeutic mechanisms of natural alkaloids in epilepsy treatment.

Language: Английский

Citations

1
Mapping the Antimicrobial Activity of Indoloquinoline and Neocryptolepine Analogues DOI Open Access
Magne O. Sydnes,

Marte Albrigtsen,

Katja S. Håheim

et al.

Heterocycles, Journal Year: 2023, Volume and Issue: 106(9), P. 1559 - 1559

Published: Jan. 1, 2023

A range of naturally occurring indoloquinolines, such as neocryptolepine and isocryptolepine, have been found to possess antimicrobial anticancer activity.To broaden our understanding this class compound´s biological capacity we herein report the results a screening campaign total 9 11H-indolo[3,2-c]quinolines, 19 analogues, two isocryptolepine analogues towards panel both Gram-positive (Enterococcus faecialis, Staphylococcus aureus, Streptococcus agalactiae) Gramnegative (Escherichia coli Pseudomonas aeruginosa) bacteria.The compounds were also tested for their cytotoxicity against human liver cells (HepG2) fetal lung fibroblast (MRC-5).Several showed cytotoxic activity, making them interesting further optimization or agents.The indoloquinolines (1) (2) (Figure 1) belongs tetracyclic N-heterocycles that are commonly in natural products, 1 agrochemicals, 2 drug candidates. 3Due vast activity possessed by group there has great interest developing synthetic strategies preparation. 1,4The broad variety pharmacological properties therefore warrants exploration. 1,5Particular is some derivatives methicillin-resistant aureus (MRSA), bacterial infection hampered increasing antibiotic resistance, unresponsive many broad-spectrum βlactam antibiotics, 6 drug-resistant biofilms, which rapidly becoming global health threat. 7

Language: Английский

Citations

2
Synergistic Lewis–Brønsted Acid Catalysis in Cascade Cyclization of ortho-Alkynylaryl Cyclopropylketones for the Synthesis of 2,3-Dihydronaphtho[1,2-b]furans DOI

Kanokwan Jaithum,

Charnsak Thongsornkleeb, Jumreang Tummatorn

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(22), P. 15358 - 15379

Published: Oct. 25, 2022

In this work, a synthetic method for the synthesis of 2,3-dihydronaphtho[1,2-b]furans employing synergistic Lewis-Brønsted Acid catalyzed cyclization ortho-alkynylarylcyclopropylketones has been developed. Benefits our included low catalyst loading, cost catalyst, short reaction time, and mild conditions which could be applied to broad range substrates, including terminal alkyne (R = H), provide generally high yields desired products. addition, we found that 2,3-dihydronaphtho[1,2-b]furan derivatives isomerized give 5,6-dihydrotetraphen-7-ol anaologs under acidic via Friedel-Crafts-type alkylation in good excellent yields. However, these products were not stable gradually converted corresponding quinones. The competent transformation was successfully obtained by treating with m-CPBA presence NaHCO3 quinone

Language: Английский

Citations

3
Six-membered ring systems: pyridines and benzo derivatives DOI

Jeanese C. Badenock

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 383 - 425

Published: Jan. 1, 2023

Language: Английский

Citations

1
Indoloquinoline Alkaloids as Antimalarials: Advances, Challenges, and Opportunities DOI Creative Commons
Prakash T. Parvatkar,

Khaly Diagne,

Yingzhao Zhao

et al.

ChemMedChem, Journal Year: 2024, Volume and Issue: unknown

Published: June 6, 2024

Abstract Malaria infections affect almost half of the world‘s population, with over 200 million cases reported annually. Cryptolepis sanguinolenta , a plant native to West Africa, has long been used across various regions Africa for malaria treatment. Chemical analysis revealed that is abundant in indoloquinolines, which have shown possess antimalarial properties. Cryptolepine, neocryptolepine, and isocryptolepine are well‐studied indoloquinoline alkaloids known their potent activity. However, structural rigidity associated cellular toxicity major drawbacks preclinical development. This review focuses on potential (cryptolepine, isocryptolepine) as scaffolds drug discovery. The article delves into effects vitro vivo, well proposed mechanisms action structure‐activity relationship studies. Several studies aim improve these leads by reducing cytotoxicity while preserving or enhancing activity gaining insights action. These investigations highlight indoloquinolines scaffold developing new drugs.

Language: Английский

Citations

0