{"id":61012,"date":"2024-09-30T11:50:07","date_gmt":"2024-09-30T11:50:07","guid":{"rendered":"https:\/\/biomedpharmajournal.org\/?p=61012"},"modified":"2024-10-09T17:33:13","modified_gmt":"2024-10-09T17:33:13","slug":"exploring-the-versatility-of-ferrocene-and-its-derivatives-a-comprehensive-review","status":"publish","type":"post","link":"https:\/\/biomedpharmajournal.org\/staging\/vol17no3\/exploring-the-versatility-of-ferrocene-and-its-derivatives-a-comprehensive-review\/","title":{"rendered":"Exploring the Versatility of Ferrocene and its Derivatives: A Comprehensive Review"},"content":{"rendered":"\n

Introduction<\/strong><\/strong><\/p>\n\n\n\n

Organometallics\nare the metallic complexes of organic compounds. Organometallics have a greater\ndiversity of stereochemistry than organic compounds, ranging from linear to\noctahedral and even beyond (30 stereoisomers exist for an octahedral complex\nwith six different ligands). Kinetic properties of the organometallics can be\ncontrolled using rational ligand design. Additionally, their metal atoms have a\nlow oxidation state, without any charges, are kinetically stable, and are\nhighly lipophilic. Organometallic compounds offer abundant opportunities for\ncreating innovative categories of pharmaceutical compounds, potentially\nshowcasing distinctive mechanisms of action specific to metals. This arises\nfrom their fundamental distinctions compared to traditional coordination metal\ncomplexes1<\/sup>.<\/p>\n\n\n\n

Organometallics\nemployed for medical applications contain Fe, Ru, Co, Zr, Pt, Ti, V, Nb, and\nMo. Among them, platinum compounds are most commonly employed. Despite enormous\nsuccess, platinum compounds have two major side effects: they are ineffective\nagainst platinum-resistant tumors and have serious adverse effects, such as\nnephrotoxicity. The latter drawback arises from the medication’s focal point\nbeing DNA, a ubiquitous component in all cells. Furthermore, due to the\nparticular chemical structure of platinum complexes, there are few\nopportunities for rational improvements that could increase its tumor\nspecificity and lower undesirable side effects2<\/sup>. In contrast, ferrocene has fewer side\neffects and can be used to prevent platinum-resistant tumors. Historically,\nferrocene’s therapeutic potential has been studied because it was the first\norganometallic substance for which anti-proliferative effects were noted2,3<\/sup>.<\/p>\n\n\n\n

Ferrocene<\/strong><\/strong><\/p>\n\n\n\n

Ferrocene (Figure 1) was first identified in 19514,5<\/sup>. Later, Wilkinson and co-workers, and Goermen and co-workers determined its precise structure6,7<\/sup>. Woodward and co-workers named these novel iron compounds ferrocene because of their similarity with benzene8<\/sup>. Modern organometallic chemistry was founded as a result of the elucidation of the ferrocene molecule\u2019s structure, which was a significant discovery in the history of chemistry. Today, the words “sandwich compound” and “metallocene” describe a considerably wider variety of compounds containing various metals in addition to ferrocene and its derivatives9<\/sup>. Due to its intriguing chemistry, ferrocene immediately caught the interest of the scientific and technical world9,10<\/sup>. Without delay, chemists began to develop synthetic approaches that developed ferrocene derivatives and explored their uses in various scientific fields11<\/sup>. Ferrocene has several applications in materials science, including sensors12-21<\/sup>, catalysts19,22-27<\/sup>, electroactive materials28-33<\/sup>, and aerospace materials34-35<\/sup>, because of its advantageous electrical characteristics and ease of functionalization. Ferrocenes are well-liked molecules for biological applications due to their stability in aqueous and aerobic media and their variety of possible derivatives35-42<\/sup>.<\/p>\n\n\n\n

There are ongoing\nstudies on the uses of ferrocenes in pharmaceutical applications. Numerous\nstudies have demonstrated that some ferrocene derivatives are highly effective\nboth in vitro and in vivo against a variety of diseases, including bacterial\nand fungal infections43-44<\/sup>,\nmalaria40, 45-47<\/sup>,\nhuman immunodeficiency virus (HIV) infection48<\/sup>, and cancer36-42<\/sup>. The anticancer\nefficacy of ferrocene compounds having amine or amide groups against\nlymphocytic leukemia P-388.48 led Brynes and coworkers49<\/sup> to report the\nanticancer potential of ferrocene derivatives in the late 1970s.  Since\nthen, different ferrocene compounds have been synthesized and their anticancer\nabilities were evaluated. Ge\nX and coworkers50<\/sup> studied ferrocene appended iridium (III) complexes\nfor anticancer activity. Shen-Zhen Ren and coworkers synthesized and evaluated COX-2 inhibition\nactivity of ferrocene-pyrazole derivatives51<\/sup>. Ferrocene-modified analogs such\nas ferrocene phenol hybrid52<\/sup>, Imatinib and Nilitinib53<\/sup>\nhave been studied for anticancer activity. <\/p>\n\n\n\n

It was\nsignificant enough to demonstrate that adding a ferrocene group to the right\ncarrier might increase an agent’s antitumor activity. <\/p>\n\n\n\n\n\n
\"\"<\/td>\n\n

Figure 1:<\/strong> Ferrocene<\/strong>.<\/strong><\/p>\n

<\/p>\n

Click here to view Figure<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

Ferrocene Derivatives<\/strong><\/p>\n\n\n\n

Formyl Derivative of Ferrocene<\/strong><\/p>\n\n\n\n

Tang J54<\/sup>\nsynthesized Formyl ferrocene through the reaction of ferrocene, CH(OEt)3<\/sub>, and anhydrous\nsolvent \n \n \n \n
\n(anhydrous\nAlCl3<\/sub>), followed by stirring to obtain the desired product.<\/p>\n\n\n\n\n\n
\"\"<\/td>\n\n

Scheme 1:<\/strong> Synthesis of Formyl Ferrocene<\/strong><\/p>\n

<\/p>\n

Click here to view Scheme<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

Chalcone Derivative of Formyl Ferrocene<\/strong><\/p>\n\n\n\n

Song QB55<\/sup> synthesized ferrocene chalcone derivatives (Scheme 2). To synthesize compound 3, formyl ferrocene underwent a reaction with bromoacetophenone (2). Subsequently, compound 3 was subjected to treatment with Pd (0) and ArB(OH)2<\/sub>, resulting in the formation of compounds 4a-4c. Various derivatives can be synthesized by using substituted Ar.<\/p>\n\n\n\n\n\n
\"\"<\/td>\n\n

Scheme 2:<\/strong> Synthesis of Chalcone derivatives of Formyl Ferrocene<\/strong><\/p>\n

<\/p>\n

Click here to view Figure<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

Alternatively, acetyl ferrocene (5) was reacted with bromobenzaldehyde (6). After this, compound 7 was treated with Pd (0) and ArB(OH)2<\/sub>, forming compound 8. Various chalcone derivatives (Scheme 3) can be synthesized by substituting Ar in ArB(OH)2<\/sub>.<\/p>\n\n\n\n\n\n
\"\"<\/td>\n\n

Scheme 3:<\/strong> Synthesis of Chalcone derivatives of Acetyl Ferrocene<\/strong><\/p>\n

<\/p>\n

Click here to view Scheme<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

Furan Containing Derivatives of Ferrocene<\/strong><\/p>\n\n\n\n

Moynahan EB56 <\/sup>successfully produced Ferrocene derivatives incorporating a furan ring (Table 1). The condensation of ferrocene carboxy hydrazide with 5-nitro-2-furaldehyde and 5-nitro-2-acetylfuran led to compounds 9a and 9b, respectively. Ferrocene carboxy hydrazide was condensed with ethyl-5-nitro-2-furimidate hydrochloride, resulting in the synthesis of N-ferrocenecarboxamido-5-nitro-2-furamidine, designated as compound 10.<\/p>\n\n\n\n

Acetylferrocene readily undergoes condensation with 2-furan aldehyde and 5-methyl-2-furaldehyde, forming compounds 11a and 11b, respectively. However, this reaction failed under various conditions with 5-nitro-2-furanaldehyde to yield 11c. Alternatively, ferrocene carboxaldehyde can be condensed with 2-acetylfuran and 2-acetyl-5-nitrofuran, producing compounds 12a and 12b respectively, which are isomeric to 11a and 11c.<\/p>\n\n\n\n

The reaction of compounds 11a, 12a, and 12b with phenylhydrazine resulted in the formation of pyrazolines 13, 14a, and 14b, respectively55<\/sup>. However, when chalcone 12a was subjected to a reaction with phenylhydrazine at room temperature, a compound presumed to be 15 was obtained instead of the expected pyrazoline 14a.<\/p>\n\n\n\n\n\n
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Table 1: <\/strong>Reactants for furan derivatives of ferrocene<\/strong><\/p>\n

<\/p>\n

Click here to view Table<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

The reaction of hydrazine or acetyl hydrazine with 11a led to pyrazoline 16a or 16b formation. Reaction of isomeric chalcones 12a\/12b with hydrazine led to pyrazoline 17a\/17b56<\/sup>.<\/p>\n\n\n\n

Cholesterol Derivative of Ferrocene<\/strong><\/p>\n\n\n\n

Cholesterol derivatives of ferrocene were synthesized by Lewkowski J and co-workers57 <\/sup>in 2004 and then by V\u00e1radi M, and Skoda-F\u00f6ldes R58<\/sup> in 2022. \u03b1-(Ferrocenyl)-amino methane phosphonous acid derivatives (19a-19d) were synthesized by joining the steroid moiety and the ferrocene group with the help of amino phosphonous acid (Scheme 4).<\/p>\n\n\n\n\n\n
\"\"<\/td>\n\n

Scheme 4: <\/strong>Synthesis of Cholesterol derivatives of Ferrocene<\/strong><\/p>\n

<\/p>\n

Click here to view Scheme<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

Diester Derivative of Ferrocene<\/strong><\/p>\n\n\n\n

1,1′-Bis-(chlorocarbonyl)ferrocene (20) derivatives were synthesized by Medina59<\/sup>. 20 after reaction with cholesterol in the presence of benzene and triethylamine, resulted in the formation of 1,1′-diester cholesterol derivative (21).<\/p>\n\n\n\n\n\n
\"\"<\/td>\n\n

Scheme 5:<\/strong> Synthesis of Diester derivatives of Ferrocene<\/strong><\/p>\n

<\/p>\n

Click here to view Scheme<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

Steroid Derivative of Ferrocene<\/strong><\/p>\n\n\n\n

Estradiol after esterification (22) with dicarboxylic acid (succinic acid) was converted to 17\u03b2- hemisuccinate (24).  Cais M60 <\/sup>used amino methyl ferrocene (23) as a conjugating reagent to form an amide bond with the carboxylic acid. <\/p>\n\n\n\n\n\n
\"\"<\/td>\n\n

Scheme 6:<\/strong> Synthesis of Steroid derivatives of Ferrocene<\/strong><\/p>\n

<\/p>\n

Click here to view Scheme<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

Steroid Derivative of Ferrocene with Glycine as Linker Group and with Two Cholesteryl Groups<\/strong><\/p>\n\n\n\n

Utilizing an N-protected glycine ester, product 25 was synthesized via the acylation of cholesterol. Subsequently, following the removal of the protecting group, the amino derivative 26 was linked to ferrocene derivatives 1-chlorocarbonyl ferrocene(27) and 1,1\u2032-bis(chlorocarbonyl)ferrocene (20) through an amide bond, resulting in the formation of conjugates 28 and 29, respectively61<\/sup>.<\/p>\n\n\n\n\n\n
\"\"<\/td>\n\n

Scheme 7:<\/strong> Synthesis of Steroid derivatives of Ferrocene with glycine as a linker group and two cholesteryl groups<\/strong><\/p>\n

Click here to view Scheme<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

Similarly, compound 32 containing two cholesteryl moieties was produced starting from 1,1\u2032-bis(chlorocarbonyl)ferrocene 2062<\/sup>.<\/p>\n\n\n\n\n\n
\"\"<\/td>\n\n

Scheme 8:<\/strong> Synthesis of Steroid derivatives of Ferrocene with two cholesteryl groups.<\/strong><\/p>\n

<\/p>\n

Click here to view Scheme<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

1-chlorocarbonyl ferrocene (27) after reaction with diamino alkane gave 33, which after reaction with 30 yielded 3463<\/sup>.<\/p>\n\n\n\n\n\n
\"\"<\/td>\n\n

Scheme 9:<\/strong> Synthesis of steroid derivatives of Ferrocene with amino moiety as the linker group<\/strong><\/p>\n

<\/p>\n

Click here to view Scheme<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

Conclusion<\/strong><\/p>\n\n\n\n

In conclusion, the synthesis and preparation of diverse ferrocene\nderivatives present a compelling avenue for advancing research in various\nfields, including materials science, catalysis, and medicinal chemistry. The\nversatility of ferrocene’s structural framework offers immense potential for\ntailoring properties to suit specific applications. Through innovative\nsynthetic methodologies and strategic functionalization, researchers continue\nto expand the scope of ferrocene derivatives, unlocking novel properties and\napplications. As this manuscript highlights, the systematic exploration of\nferrocene derivatives contributes significantly to advancing interdisciplinary\nresearch and holds promise for addressing complex challenges in diverse\nscientific domains. Further exploration and refinement of synthetic strategies\nwill undoubtedly lead to the discovery of new ferrocene derivatives with\nenhanced properties and functionalities, driving progress in both fundamental\nunderstanding and practical applications.<\/p>\n\n\n\n

Acknowledgement<\/strong><\/p>\n\n\n\n

The authors are grateful to the institute for the sources and facilities provided during the literature review.<\/p>\n\n\n\n

Conflict of Interest<\/strong> <\/p>\n\n\n\n

The authors do not have any conflict of interest. <\/p>\n\n\n\n

Funding Sources<\/strong><\/p>\n\n\n\n

The author(s) received no financial support for the research, authorship, and\/or publication of this article<\/p>\n\n\n\n

Data Availability Statement<\/strong><\/p>\n\n\n\n

This statement does not apply to this article.<\/p>\n\n\n\n

Ethics Statement<\/strong><\/p>\n\n\n\n

This research did not involve human participants, animal subjects, or any material that requires ethical approval.<\/p>\n\n\n\n

Informed Consent Statement<\/strong><\/p>\n\n\n\n

This study did not involve human participants, and therefore, informed consent was not required.<\/p>\n\n\n\n

References<\/strong><\/p>\n\n\n\n

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