An Improved Two-step Preparation of 2,4-Dimethylpyrrole

Meng, Guangrong; Zheng, Meilin; Wang, Mei

doi:10.1080/00304948.2011.582005

Cited by 11 publications

(3 citation statements)

References 11 publications

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“…To conjugate a photoabsorber with the Pt(IV) center, a BODIPY with a phenol moiety in the meso-position of the dipyrromethene core was utilized. 2,4-Dimethyl pyrrole was obtained in two consecutive steps following the previously published procedures. , BODIPY 3 with a phenol functional group was obtained by the reaction of pyrrole 2 with p -hydroxybenzaldehyde . The first method to synthesize a Pt(IV) prodrug with BODIPY in the axial position was based on the formation of a carbamate linkage between the Pt(IV) center and an axial ligand.…”

Section: Resultsmentioning

confidence: 99%

Light-Responsive Pt(IV) Prodrugs with Controlled Photoactivation and Low Dark Toxicity

Spector,

Bubley,

Zharova

et al. 2024

ACS Appl. Bio Mater.

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Light-induced release of cisplatin from Pt(IV) prodrugs represents a promising approach for precise control over the antiproliferative activity of Pt-based chemotherapeutic drugs. This method has the potential to overcome crucial drawbacks of conventional cisplatin therapy, such as high general toxicity toward healthy organs and tissues. Herein, we report two Pt(IV) prodrugs with BODIPY-based photoactive ligands Pt-1 and Pt-2, which were designed using carbamate and triazole linkers, respectively. Both prodrugs demonstrated the ability to release cisplatin under blue light irradiation without the requirement of an external reducing agent. Dicarboxylated Pt-2 prodrug turned out to be more stable in the dark and more sensitive to light than its monocarbamate Pt-1 counterpart; these observations were explained using DFT calculations. The investigation of the photoreduction mechanism of Pt-1 and Pt-2 prodrugs using DFT modeling and ΔG 0 PET estimation suggests that the photoinduced electron transfer from the singlet excited state of the BODIPY axial ligand to the Pt(IV) center is the key step in the light-induced release of cisplatin from the complexes. Cytotoxicity studies demonstrated that both prodrugs were nontoxic in the dark and toxic to MCF-7 cells under low-dose irradiation with blue light, and the observed effect was solely due to the cisplatin release from the Pt(IV) prodrugs. Our research presents an elegant synthetic approach to light-activated Pt(IV) prodrugs and presents findings that may contribute to the future rational design of photoactivatable Pt(IV) prodrugs.

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Section: Resultsmentioning

confidence: 99%

Light-Responsive Pt(IV) Prodrugs with Controlled Photoactivation and Low Dark Toxicity

Spector,

Bubley,

Zharova

et al. 2024

ACS Appl. Bio Mater.

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“…All yields reported are of isolated materials judged to be homogeneous using TLC and NMR spectroscopy. Aryldiazonium tetrafluoroborates, HMF, , and 2,4-dimethylpyrrole were synthesized by a reported procedure. (Aminomethyl)polystyrene (70–90 mesh, 1% cross-linked) was purchased from Sigma-Aldrich.…”

Section: Methodsmentioning

confidence: 99%

5-Hydroxymethylfurfural-Derived Boron-Dipyrromethene Immobilized on Resin Support as a Sustainable Catalyst for C–H Arylation of Heterocycles

2019

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5-Hydroxymethylfurfural (HMF) was used as a sustainable raw material in the development of a resin-supported boron-dipyrromethene (BODIPY)-based photocatalyst. In the development of the catalyst, the brominated product (HMF-BODIPY-Br) and photocatalyst (HMF-BODIPY-Br-Suc) were isolated under a chromatography-free condition. The photocatalyst was loaded on polymeric resin by bridging alcohol functionality in HMF and amine functionality in polymeric resin using succinic anhydride. The resin-supported photocatalyst was used in light-mediated C–H arylation of various heterocycles using aryldiazonium salt. For representative examples, diazotization and photoarylation were carried out in one pot, and arylated furans were obtained in very good yields. C–H arylation was found to proceed via a photogenerated radical intermediate, and the radical intermediate was trapped by forming an adduct with TEMPO.

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“…The authors have cited additional references within the Supporting Information. [53][54][55][56][57][58][59][60][61][62][63][64][65][66][67][68][69][70][71][72]…”

Section: Supporting Informationmentioning

confidence: 99%

Carbonylation as a Key Step in New Tandem Reactions – A Route to BODIPYs

Miller,

Impelmann,

Bauer

et al. 2024

Chemistry A European J

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Herein, a highly efficient five‐step reaction sequence to BODIPYs is presented. The key step is the combination of transition metal‐catalyzed in‐situ generation of aldehydes and their subsequent organocatalytic activation to yield dipyrromethanes, which are further converted to the corresponding BODIPY. Classic syntheses towards BODIPYs have relied on aldehydes or acid chlorides, which are often not commercially available and rather sensitive to handle. The presented approach starts from readily available and stable alkenes or aryl‐bromides, which allows to extend the range of readily available BODIPYs that can be tailored for their specific use. The synthesis of 55 derivatives with overall yields of up to 78% demonstrates the wide applicability and advantages of the presented method.

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An Improved Two-step Preparation of 2,4-Dimethylpyrrole

Cited by 11 publications

References 11 publications

Light-Responsive Pt(IV) Prodrugs with Controlled Photoactivation and Low Dark Toxicity

Light-Responsive Pt(IV) Prodrugs with Controlled Photoactivation and Low Dark Toxicity

5-Hydroxymethylfurfural-Derived Boron-Dipyrromethene Immobilized on Resin Support as a Sustainable Catalyst for C–H Arylation of Heterocycles

Carbonylation as a Key Step in New Tandem Reactions – A Route to BODIPYs

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