Synthesis and biological evaluation of 2-(4-methylsulfonyl phenyl) indole derivatives: multi-target compounds with dual antimicrobial and anti-inflammatory activities

Shaker, Ahmed; Abdelall, Eman K. A.; Abdellatif, Khaled R.A.; Abdel‐Rahman, Hamdy M.

doi:10.1186/s13065-020-00675-5

Cited by 27 publications

(5 citation statements)

References 30 publications

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“…Reviewing the synthesis methods of 2-phenylindole compounds over the past two decades is indeed valuable for researchers looking to develop new indole-based drugs. The wide utilization of the 2-phenylindole skeleton in studying anticancer, bacteriostatic, and anti-inflammatory activities underscores its importance in drug discovery and development. ,,− By examination of various synthesis approaches outlined in the literature, researchers can gain insights into efficient and sustainable methods for producing these pharmacologically significant compounds, facilitating the exploration of novel indole-based therapeutic agents.…”

Section: Discussionmentioning

confidence: 99%

Comprehensive Analysis on the Synthesis Methods of 2-Phenylindole Derivatives with Pharmacological Importance for Green Synthesis

Wu,

Shen,

Zhao

et al. 2024

Org. Process Res. Dev.

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2-Phenylindoles, as a special subset of indole compounds, stand out as some of the most promising candidates for drug development. To guide researchers toward developing new 2-phenylindole drugs in a more environmentally friendly and costeffective manner, we have summarized and analyzed synthesis methods for 2-phenylindole over the past two decades. Our key findings are as follows: First, among the two methods discussed in this paper, the one-step method is often suitable for the synthesis of 2-phenylindole derivatives with a small amount of substitutions on both sides, whereas the indole C-2 coupling reaction is preferable for indole or C-2 benzene rings with more complex substitutions. Second, the primary challenge in synthesizing 2phenylindole compounds lies in achieving selectivity at the indole C-2 and C-3 sites. Lastly, to achieve more efficient, economical, and environmentally friendly methods, researchers have developed new catalytic systems, including nontoxic catalysts, metal-free catalysts, recyclable metal catalysts, or nanocrystallized transition metals, as well as new methodologies such as photoinduced reactions, electrocatalytic reactions, magnetocatalytic methods, and aqueous-phase catalytic methods. These avenues may represent future research directions for chemists. In conclusion, there remains ample room for research and development in the green synthesis of 2-phenylindole derivatives.

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Section: Discussionmentioning

confidence: 99%

Comprehensive Analysis on the Synthesis Methods of 2-Phenylindole Derivatives with Pharmacological Importance for Green Synthesis

Wu,

Shen,

Zhao

et al. 2024

Org. Process Res. Dev.

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“…Moreover, triazoles and sulfonamides are important fragments present in the structure of marketed small molecule drugs with a wide range of bioactivities such as antibacterial, analgesic, anti-inflammatory, anti-tumor, and antiviral activities, and thus possess excellent pharmacological applications. (Haider et al, 2013;Abdellatif et al, 2016;Bonandi et al, 2017;Akgul et al, 2018;Pandit et al, 2018;Bozorov et al, 2019;Zhang, 2019;Shaker et al, 2020;Zhang et al, 2021b;Dai et al, 2022;Du et al, 2023). Therefore, we hypothesized that the introduction of azido and sulfonyl groups to the simplified structure of akuammiline alkaloid picrinine might result in improved and complementary anti-RA effects.…”

Section: Introductionmentioning

confidence: 95%

Akuammiline alkaloid derivatives: divergent synthesis and effect on the proliferation of rheumatoid arthritis fibroblast-like synoviocytes

et al. 2023

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During the past decades, rheumatoid arthritis had become a serious problem, torturing millions of patients because of unclear pathogenesis and no ideal therapies. Natural products remain an important source of medicines to treat various major diseases such as rheumatoid arthritis (RA) given their excellent biocompatibility and structural diversity. Herein, we have developed a versatile synthetic method for constructing various skeletons of akuammiline alkaloid analogs based on our previous research on the total synthesis of the related indole alkaloids. We have also evaluated the effect of these analogs on the proliferation of RA fibroblast-like synoviocytes (FLSs) in vitro and analyzed the corresponding structure-activity relationship (SAR). Among these analogs, compounds 9 and 17c have demonstrated a promising inhibitory effect on the proliferation of RA-FLSs, with IC50 values of 3.22 ± 0.29 μM and 3.21 ± 0.31 μM, respectively. Our findings provide a solid foundation for future pharmacological studies on akuammiline alkaloid derivatives and inspiration for the development of anti-RA small molecule drugs derived from natural products.

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“…The results of anti‐inflammatory activity confirmed that compound (5‐fluoro‐1 H ‐indol‐2‐yl)(4‐(4‐hydroxyphenyl)piperazin‐1‐yl)methanone exhibited excellent inhibitory effect against the COX‐2 enzyme. Shaker and co‐workers [102] continue their investigations on a series of novel indole ( 61 ) derivatives as anti‐inflammatory agents. The synthesized derivatives were evaluated for their anti‐inflammatory and COX inhibitory activities.…”

Section: Bioactivity Evaluationmentioning

confidence: 99%

The Multi‐Pharmacological Targeted Role of Indole and its Derivatives: A review

Mathada¹,

Yernale

Basha³

2023

ChemistrySelect

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Heterocycles are a privileged motif that appears as a momentous objective in medicinal chemistry. An important class of compounds for drug discovery and design is indole and its derivatives, which have been examined for a variety of biological activities. Therefore, it is noteworthy in the modern progress of synthetic, medicinal chemistry; the last decade has been onlooker with a multitude of reports on several indole derivatives corroborating these chemical entities to be a renowned target for the discovery of new drugs. The current study includes brief natural sources of indole, and a new range of commercially available indole‐based drugs. Additionally, this review discusses the numerous facets of the structure‐activity relationship study (SARs) and provides information about the varied pharmacological effects of indole derivatives. The literature data presented for the anti‐pharmacological agents herein covers largely from the year 2015 to mid of 2022.

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Synthesis and biological evaluation of 2-(4-methylsulfonyl phenyl) indole derivatives: multi-target compounds with dual antimicrobial and anti-inflammatory activities

Cited by 27 publications

References 30 publications

Comprehensive Analysis on the Synthesis Methods of 2-Phenylindole Derivatives with Pharmacological Importance for Green Synthesis

Comprehensive Analysis on the Synthesis Methods of 2-Phenylindole Derivatives with Pharmacological Importance for Green Synthesis

Akuammiline alkaloid derivatives: divergent synthesis and effect on the proliferation of rheumatoid arthritis fibroblast-like synoviocytes

The Multi‐Pharmacological Targeted Role of Indole and its Derivatives: A review

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