TBA−Br and Selectfluor Mediated Bromination of Glycals and Heterocyclic Compounds: Substrate Scope and Synthetic Utility DOI

Mittali Maheshwari,

Nazar Hussain

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(38)

Published: Oct. 11, 2023

Abstract Herein, we have devised a metal‐free stereoselective protocol mediated by selectfluor for the dibromination of sugar enol‐ethers and monobromination heterocyclic compounds. The glycals was achieved within 5 minutes at room temperature with excellent yields. tolerance various protecting groups such as acetyl, benzyl, silyl in sugars checked. When same reagent system applied to substituted indoles chromones 3‐brominated products were obtained but elevated temperatures. synthetic utility methodology demonstrated using brominated synthesize 3‐aryl isoflavones respectively via Suzuki‐Miyura cross‐coupling reactions.

Language: Английский

Total syntheses and antibacterial evaluations of cudraflavones A-C and related Flavones DOI
Hongbo Dong, Li Liao,

Pei Yu

et al.

Bioorganic Chemistry, Journal Year: 2023, Volume and Issue: 140, P. 106764 - 106764

Published: Aug. 9, 2023

Language: Английский

Citations

14

Total Syntheses and Antibacterial Studies of Natural Isoflavones: Scandenone, Osajin, and 6,8-Diprenylgenistein DOI Creative Commons
Hongbo Dong,

Yufei Che,

Xingtong Zhu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(11), P. 2574 - 2574

Published: May 30, 2024

Isoflavones are a class of natural products that exhibit wide range interesting biological properties, including antioxidant, hepatoprotective, antimicrobial, and anti-inflammatory activities. Scandenone (1), osajin (2), 6,8-diprenylgenistein (3) prenylated isoflavones share the same polyphenol framework. In this research, key intermediate 15 was used for synthesis 1–3, establishing stereoselective synthetic method both linear angular pyran isoflavones. The antibacterial activities 1–3 were also evaluated, all them displayed good activity against Gram-positive bacteria. Among them, 2 most potent one MRSA, with MIC value μg/mL, SEM assay indicated bacterial cell membranes MRSA E. faecalis could be disrupted by 2. These findings suggest type isoflavone serve as lead development novel agents treatment infections.

Language: Английский

Citations

5

Total synthesis of isoflavonoids DOI Creative Commons
Mamoalosi A. Selepe,

Siyanda T. Mthembu,

Molahlehi S. Sonopo

et al.

Natural Product Reports, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The review is on synthesis of different classes isoflavonoids that include isoflavones, isoflavanones, isoflavans, isoflavenes, pterocarpans, rotenoids, coumaronochromones, and coumestans.

Language: Английский

Citations

0

N‐Heterocyclic Carbene Organocatalysis Enabled Modular Synthesis of Fluorinated Isoflavonoids to Suppress Proliferation and Migration in Breast Cancer Cells DOI Creative Commons
Yanqing Liu, Leilei Fu,

Liwu Hong

et al.

Advanced Science, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 13, 2025

Abstract Isoflavonoids represent a privileged scaffold among various bioactive natural products, rendering their structural diversification through green synthesis and subsequent biological evaluations compelling research area. In this study, an NHC organocatalytic radical acylalkylation of 1,3‐enynes using salicylaldehydes is presented, followed by cascade intramolecular annulation, yielding series fluorinated isoflavone derivatives with substantial yields under environmental‐friendly conditions. This approach, distinguished its excellent modularity high functional group tolerance, represents unprecedented 1,3,4‐trifunctionalization designed for the isoflavones in single step. Furthermore, it demonstrated that these synthesized isoflavonoids effectively suppress proliferation breast cancer cells, most potent compound 8 also inhibiting migration MDA‐MB‐231 cells.

Language: Английский

Citations

0

Synthesis and Bioactivity of Isoflavones from Ficus carica and Some Non-Natural Analogues DOI
Vaderament‐A. Nchiozem‐Ngnitedem, Eric Sperlich,

Valaire Yemene Matieta

et al.

Journal of Natural Products, Journal Year: 2023, Volume and Issue: 86(6), P. 1520 - 1528

Published: May 30, 2023

Ficucaricone D (1) and its 4′-demethyl congener 2 are isoflavones isolated from fruits of Ficus carica that share a 5,7-dimethoxy-6-prenyl-substituted A-ring. Both natural products were, for the first time, obtained by chemical synthesis in six steps, starting 2,4,6-trihydroxyacetophenone. Key steps microwave-promoted tandem sequence Claisen- Cope-rearrangements to install 6-prenyl substituent Suzuki–Miyaura cross coupling installing B-ring. By using various boronic acids, non-natural analogues become conveniently available. All compounds were tested cytotoxicity against drug-sensitive drug-resistant human leukemia cell lines, but found be inactive. The also antimicrobial activities panel eight Gram-negative two Gram-positive bacterial strains. Addition efflux pump inhibitor phenylalanine-arginine-β-naphthylamide (PAβN) significantly improved antibiotic activity most cases, with MIC values as low 2.5 μM improvement factors high 128-fold.

Language: Английский

Citations

8

Recent Advances on Pd Schiff Base Catalysts in Suzuki-Miyaura Cross-Coupling Reaction: A Review DOI

Iman Hussein Hasan,

Raed Muslim Mhaibes,

Abdul Amir H. Kadhum

et al.

Journal of Organometallic Chemistry, Journal Year: 2024, Volume and Issue: 1024, P. 123444 - 123444

Published: Nov. 16, 2024

Language: Английский

Citations

3

Divergent Total Synthesis of Isoflavone Natural Products and Their Potential as Therapeutic Agents for TTR Amyloidosis DOI Creative Commons

Nguyen Ngoc Thanh Luan,

Takuya Okada, Takeshi Yokoyama

et al.

Journal of Natural Products, Journal Year: 2024, Volume and Issue: 87(11), P. 2604 - 2614

Published: Oct. 27, 2024

We have achieved the divergent total synthesis of nine isoflavone natural products

Language: Английский

Citations

1

Progressive Efforts in the Implementation of Integrated Water Resources Management (IWRM) in Uganda DOI
Benson Turyasingura,

Rogers Akatwijuka,

Wycliffe Tumwesigye

et al.

Disaster Resilience and Green Growth, Journal Year: 2023, Volume and Issue: unknown, P. 543 - 558

Published: Jan. 1, 2023

Language: Английский

Citations

3

Catalytic prenylation of natural polyphenols DOI Creative Commons

Yi Du,

Iman Korchi,

А. Е. Рубцов

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(44), P. 20358 - 20362

Published: Jan. 1, 2023

Prenylated polyphenols occur naturally and exhibit biological activity superior to the ubiquitous parent polyphenols.

Language: Английский

Citations

2

Structure–Activity Relationship Prediction‐Based Synthesis and Cytotoxicity Evaluation against the HEp‐2 Laryngeal Carcinoma Cell of Isoflavone–Cytisine Mannich Bases DOI Open Access
Galyna P. Mrug, Diana Hodyna, Larysa Metelytsia

et al.

Chemistry & Biodiversity, Journal Year: 2023, Volume and Issue: 20(8)

Published: July 21, 2023

QSAR analysis of previously synthesized and nature-inspired virtual isoflavone-cytisine hybrids against the HEp-2 laryngeal carcinoma cell lines was performed using OCHEM web platform. The validation models an external test set proved that can be used to predict activity newly designed compounds such as 8-cytisinylmethyl derivatives 5,7- 6,7-dihydroxyisoflavones. synthetic procedure for selective aminomethylation 5,7-dihydroxyisoflavones with cytisine developed. In vitro testing identified compound 7 f cisplatin-level cytotoxicity 10 which twice active than cisplatin after 72 h incubation.

Language: Английский

Citations

1