Visible-Light-Mediated O–H Functionalization Reactions of Acetylenic alcohols with 3-diazooxindoles: Facile Access to Spirooxindole-Fused Oxacycles DOI

Liqin Xu,

Jing Wang,

Hujin Li

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 159, P. 134014 - 134014

Published: May 3, 2024

Language: Английский

Antineoplastic indole-containing compounds with potential VEGFR inhibitory properties DOI Creative Commons

Dalia R. Aboshouk,

Mohamed A. Youssef, Mohamed S. Bekheit

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(9), P. 5690 - 5728

Published: Jan. 1, 2024

VEGF, an important category of tyrosine kinases, and its receptors (VEGFR) are hyper-activated in different cancers. The recently reported indolyl analogs with potential antineoplastic VEGFR inhibitory properties highlighted.

Language: Английский

Citations

8

C3-Spirooxindoles: Divergent chemical synthesis and bioactivities (2018–2023) DOI
Mohamed H. Helal, Medhat E. Owda,

Amal T. Mogharbel

et al.

Bioorganic Chemistry, Journal Year: 2024, Volume and Issue: 143, P. 107091 - 107091

Published: Jan. 4, 2024

Language: Английский

Citations

7

Indole-Based Compounds as Potential Drug Candidates for SARS-CoV-2 DOI Creative Commons
Adel S. Girgis, Siva S. Panda, Benson M. Kariuki

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(18), P. 6603 - 6603

Published: Sept. 13, 2023

The COVID-19 pandemic has posed a significant threat to society in recent times, endangering human health, life, and economic well-being. disease quickly spreads due the highly infectious SARS-CoV-2 virus, which undergone numerous mutations. Despite intense research efforts by scientific community since its emergence 2019, no effective therapeutics have been discovered yet. While some repurposed drugs used control global outbreak save lives, none proven universally effective, particularly for severely infected patients. Although spread of is generally under control, anti-SARS-CoV-2 agents are still needed combat current future infections. This study reviews most promising containing indolyl heterocycle, an essential scaffold many alkaloids with diverse bio-properties various biological fields. also discusses natural synthetic indole-containing compounds properties computer-aided drug design (in silico studies) optimizing hits/leads.

Language: Английский

Citations

13

Asymmetric Intramolecular Amination Catalyzed with Cp*Ir-SPDO via Nitrene Transfer for Synthesis of Spiro-Quaternary Indolinone DOI
Shiqiang Wei, Zihao Li, Shuanghu Wang

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(28), P. 18841 - 18847

Published: July 8, 2024

An asymmetric intramolecular spiro-amination to high steric hindering

Language: Английский

Citations

5

Indole Derivatives: Unveiling New Frontiers in Medicinal and Synthetic Organic Chemistry DOI Creative Commons
Faiza Saleem, Khalid Mohammed Khan

Molecules, Journal Year: 2023, Volume and Issue: 28(14), P. 5477 - 5477

Published: July 18, 2023

In recent years, significant attention has been given to indoles, a diverse group of heterocyclic compounds widely found in nature that play crucial role various bioactive natural and synthetic substances [...].

Language: Английский

Citations

10

Dearomative ipso-Cyclization to Spiropseudoindoxyls: An Extendable Approach To Access Indolo[3,2-c]quinolinones and Isocryptolepine DOI
Chada Raji Reddy,

Agnuru Theja,

Ejjirotu Srinivasu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 26(1), P. 68 - 72

Published: Dec. 31, 2023

A metal-free oxidative intramolecular dearomative spirocyclization of indole-3-formyl-2-carboxamides has been developed for the first time, affording spiropseudoindoxyls in good yields. This domino process proceeds through sequential oxidation, decarboxylation and ipso-arylation. The unique feature this approach includes compatibility N-protected-indole-2-carboxamides. Further, a hitherto unknown rearrangement to indoloquinolones achieved. synthetic utility strategy also showcased by construction natural alkaloid, isocryptolepine.

Language: Английский

Citations

10

Base controlled rongalite-mediated reductive aldol/cyclization and dimerization of isatylidene malononitriles/cyanoacetates DOI
Suryakant S. Chaudhari, Chandrakant B. Nichinde, Baliram R. Patil

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(8), P. 1727 - 1732

Published: Jan. 1, 2024

In this study, we developed a novel methodology involving base-controlled, rongalite-mediated reductive/aldol reaction, followed by cyclization of isatylidene malononitriles/cyanoacetates, resulting in the synthesis spiro[2,3-dihydrofuran-3,3'-oxindole]. Additionally, have disclosed dimerization process for malononitriles, yielding dispiro[cyclopent-3'-ene]bisoxindole. The utilization rongalite reaction serves dual purpose, acting both as reducing agent and C1 synthon. approach has several advantages like simple setup, wide substrate scope, requiring less time, using water green solvent, no metal or catalyst is required products can be easily isolated

Language: Английский

Citations

4

Indole Compounds in Oncology: Therapeutic Potential and Mechanistic Insights DOI Creative Commons
S. M. E. HASSAN, Alyaa Farid, Siva S. Panda

et al.

Pharmaceuticals, Journal Year: 2024, Volume and Issue: 17(7), P. 922 - 922

Published: July 10, 2024

Cancer remains a formidable global health challenge, with current treatment modalities such as chemotherapy, radiotherapy, surgery, and targeted therapy often hindered by low efficacy adverse side effects. The indole scaffold, prominent heterocyclic structure, has emerged promising candidate in the fight against cancer. This review consolidates recent advancements developing natural synthetic indolyl analogs, highlighting their antiproliferative activities various cancer types over past five years. These analogs are categorized based on common types, supported biochemical assays demonstrating properties. In this review, emphasis is placed elucidating mechanisms of action these compounds. Given limitations conventional therapies, therapeutics enhanced selectivity reduced effects critical focus oncological research.

Language: Английский

Citations

4

Enantioselective Total Synthesis of (−)-Caulamidine A DOI
Zhouyang Zhu, Thomas J. Maimone

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(26), P. 14215 - 14220

Published: June 21, 2023

Marine bryozoans continue to provide architecturally fascinating halogenated alkaloids that pose unique challenges for chemical synthesis. The antimalarial caulamidines A and B, recently isolated from Caulibugula intermis, contain an intricate bis-amidine core a chlorine-bearing neopentylic stereocenter. Compared topologically similar C20 bis(cyclotryptamine) alkaloids, possess additional carbon atom of unknown biosynthetic origins, which renders their entire skeleton nonsymmetric nondimeric. Herein, we report the first total synthesis caulamidine confirm its absolute configuration. Key findings include exploitation glycol bistriflate facilitate rapid, diastereoselective ketone-amidine annulation reaction highly hydrogen transfer correctly establish key stereogenic center.

Language: Английский

Citations

9

Synthesis of Tetracyclic Spirooxindolepyrrolidine-Engrafted Hydantoin Scaffolds: Crystallographic Analysis, Molecular Docking Studies and Evaluation of Their Antimicrobial, Anti-Inflammatory and Analgesic Activities DOI Creative Commons

Amani Toumi,

Faiza I. A. Abdella,

Sarra Boudriga

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(21), P. 7443 - 7443

Published: Nov. 6, 2023

In a sustained search for novel potential drug candidates with multispectrum therapeutic application, series of spirooxindoles was designed and synthesized via regioselective three-component reaction between isatin derivatives, 2-phenylglycine diverse arylidene-imidazolidine-2,4-diones (Hydantoins). The suggested stereochemistry ascertained by an X-ray diffraction study NMR spectroscopy. resulting tetracyclic heterocycles were screened their in vitro vivo anti-inflammatory analgesic activity antimicrobial potency. antibacterial screening revealed that several derivatives exhibited remarkable growth inhibition against different targeted microorganisms. All tested compounds showed excellent the Micrococccus luteus strain (93.75 µg/mL ≤ MIC 375 µg/mL) as compared to reference tetracycline (MIC = 500 µg/mL). Compound 4e bearing p-chlorophenyl group on pyrrolidine ring greatest antifungal toward Candida albicans krusei values 23.43 46.87 µg/mL, respectively) Amphotericin B 31.25 62.50 respectively). target also lipoxygenase-5 (LOX-5) enzyme. Compounds 4i 4l significant inhibitory IC50 1.09 mg/mL 1.01 mg/mL, respectively, more potent than parent drug, diclofenac sodium (IC50 1.19 mg/mL). addition, evaluation these assessed through carrageenan-induced paw edema acetic acid-induced writhing assays, revealing promising results. silico molecular docking predictive ADMET studies active spirocompounds carried out.

Language: Английский

Citations

9