Thionation of Some α,β-Unsaturated Steroidal Ketones

Krstić, Natalija M.; Bjelaković, Mira S.; Dabović, Milan; Pavlović, Vera P.

doi:10.3390/molecules15053462

Cited by 21 publications

(13 citation statements)

References 26 publications

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“…Hence, the dimerization strategy was applied to steroids with the goal of improving their biological potential. Several dimers were fabricated by reaction of steroidal compounds ( 1a – d ) with Lawesson’s catalyst [ 8 ]. According to the reaction conditions, different proportions of the dimers 2 , 3, and 4 with distinct linkers were isolated and characterized ( Figure 2 ).…”

Section: Steroids Dimers and Non-steroidal Analogsmentioning

confidence: 99%

Recent Advances in the Use of the Dimerization Strategy as a Means to Increase the Biological Potential of Natural or Synthetic Molecules

2021

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The design of C2-symmetric biologically active molecules is a subject of interest to the scientific community. It provides the possibility of discovering medicine with higher biological potential than the parent drugs. Such molecules are generally produced by classic chemistry, considering the shortness of reaction sequence and the efficacy for each step. This review describes and analyzes recent advances in the field and emphasizes selected C2-symmetric molecules (or axial symmetric molecules) made during the last 10 years. However, the description of the dimers is contextualized by prior work allowing its development, and they are categorized by their structure and/or by their properties. Hence, this review presents dimers composed of steroids, sugars, and nucleosides; known and synthetic anticancer agents; polyphenol compounds; terpenes, known and synthetic antibacterial agents; and natural products. A special focus on the anticancer potential of the dimers transpires throughout the review, notwithstanding their structure and/or primary biological properties.

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Section: Steroids Dimers and Non-steroidal Analogsmentioning

confidence: 99%

Recent Advances in the Use of the Dimerization Strategy as a Means to Increase the Biological Potential of Natural or Synthetic Molecules

2021

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“…The introduction of the S atom relative to oxygen increases the reactivity of the thione functional group due to conformational changes in the modified molecule. The previous works on steroid compounds were further modified as biologically active molecules of new thioxosteroid derivatives by Natalija et al [108].…”

Section: Synthesis Of Biologically Active Steroids and Terpenoidsmentioning

confidence: 99%

“…Scheme 34 illustrates the reaction pathway in refluxing toluene for 8 h to form unstable α,β-unsaturated thioketones (109), which dimerizes to subsequent dimer sulfides (108) or decomposes to starting ketones (more stable).…”

Section: Synthesis Of Biologically Active Steroids and Terpenoidsmentioning

confidence: 99%

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

Khatoon

Abdulmalek

2021

Molecules

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Lawesson’s reagent (LR) is a well-known classic example of a compound with unique construction and unusual chemical behavior, with a wide range of applications in synthetic organic chemistry. Its main functions were rounded for the thionation of various carbonyl groups in the early days, with exemplary results. However, the role of Lawesson’s reagent in synthesis has changed drastically, and now its use can help the chemistry community to understand innovative ideas. These include constructing biologically valuable heterocycles, coupling reactions, and the thionation of natural compounds. The ease of availability and the convenient usage of LR as a thionating agent made us compile a review on the new diverse applications on some common functional groups, such as ketones, esters, amides, alcohols, and carboxylic acids, with biological applications. Since the applications of LR are now diverse, we have also included some new classes of heterocycles such as thiazepines, phosphine sulfides, thiophenes, and organothiophosphorus compounds. Thionation of some biologically essential steroids and terpenoids has also been compiled. This review discusses the recent insights into and synthetic applications of this famous reagent from 2009 to January 2021.

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“…Since the discovery of cisplatin, to this day, a large number of metal complexes have been synthesized in order to find potential chemotherapeutics with better antitumor potential, higher selectivity in killing cancer cells and fewer side effects. 26 Motivated by aforementioned issues and as a continuation of our work on the new hetero-steroid derivatives as biologically active molecules, 1,21,[27][28][29][30] we decided to prepare new steroidal complexes with platinum, in the reaction of previously synthesized 3-thiosemicarbazones 2a and 2b with cisplatin and to examine their biological activity and compare it with the activity of those reported earlier. 21 To the best of our knowledge, very few Pt steroidal complexes have been prepared so far.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones

Čobeljić

Živković

Matić

et al. 2021

JSCS

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In this work, Pt(II) complexes of previously synthesized steroidal thiosemicarbazones were synthesized and characterized. The ligands and their metal complexes were studied by analytical and spectroscopic data (elemental analysis, IR, 1D NMR and 2D NMR, HSQC, HMBC, NOESY, COSY), the analysis of which enabled complete 1H and 13C assignments of each compound including E and Z isomers. All the synthesized ligands and complexes were screened for their cytotoxic and antimicrobial activity. The results demonstrate that new steroidal thiosemicarbazone complexes were significantly less cytotoxic than corresponding steroidal thiosemicarbazones. Also, complexes show lower antimicrobial activity than the standard drugs, similar to the activity of the starting thiosemicarbazones.

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Thionation of Some α,β-Unsaturated Steroidal Ketones

Cited by 21 publications

References 26 publications

Recent Advances in the Use of the Dimerization Strategy as a Means to Increase the Biological Potential of Natural or Synthetic Molecules

Recent Advances in the Use of the Dimerization Strategy as a Means to Increase the Biological Potential of Natural or Synthetic Molecules

A Focused Review of Synthetic Applications of Lawesson’s Reagent in Organic Synthesis

Synthesis, characterization and biological activity of Pt(II) complexes with steroidal thiosemicarbazones

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