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BT - Comprehensive Heterocyclic Chemistry

T1 - Synthesis of fused heterocycles via Pd-catalyzed multiple aromatic C-H activation reactions

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JO - Chemistry of Heterocyclic Compounds

N2 - Recent developments in the synthesis of fused heterocycles using Pd-catalyzed multiple aromatic C-H activation is discussed in this highlight.

T2 - Chemistry of Heterocyclic Compounds

(2017)SYNTHESIS OF THIOPHENE-CONTAINING HETEROCYCLES AND THEIR APPLICATION AS ANTICANCER AGENTS. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

JF - Chemistry of Heterocyclic Compounds

Synthesis of N -Heterocycles - Organic chemistry

Texts:
Joule and Mills, "Heterocyclic Chemistry"
Ishihara, Montero, and Baran, "The Portable Chemist's Consultant: A Survival Guide for Discovery, Process, and Radiolabeling"

AB - Recent developments in the synthesis of fused heterocycles using Pd-catalyzed multiple aromatic C-H activation is discussed in this highlight.

Synthesis of Heterocycles - Chemistry

Five-membered heterocycles represent a privileged scaffold in drug discovery and are the focus of analog design. The first chapter presents the synthesis and biological evaluation of analogs of NSC 652287, which targets the renal carcinoma cell line A498. The Pd-catalyzed Suzuki-Miyaura cross-coupling with halogenated furan, thiophene, and selenophene led to generally high overall yields for the construction of heterocyclic triads. C-H bond activation provided an efficient strategy for the Pd-catalyzed cross-coupling at C(2) of oxazoles. Further analog variation was achieved with a copper-catalyzed azide-alkyne cycloaddition to form a 1,4-substituted 1,2,3-triazole. Potency and selectivity of the final hydroxymethyl products were determined in the NCI-60 cell assay. Two lead compounds were tested in vivo and compared to NSC 652287. The evaluation of these compounds continues with a thermal shift assay coupled with differential mass spectrometry for biological target identification. The chemical stability of select triads are also discussed.
The second chapter details the synthesis of thienopyridone and thienopyrimidine dione analogs as inhibitors of protein tyrosine phosphatase 4A3 (PTP4A3), an attractive anticancer target. Derivatization by photooxygenation led to a compound with a unique structural motif, high potency, and excellent selectivity towards PTP4A3. An automated synthesis strategy using Lilly’s Automated Synthesis Lab was employed for analog synthesis.

Five-membered heterocycles represent a privileged scaffold in drug discovery and are the focus of analog design. The first chapter presents the synthesis and biological evaluation of analogs of NSC 652287, which targets the renal carcinoma cell line A498. The Pd-catalyzed Suzuki-Miyaura cross-coupling with halogenated furan, thiophene, and selenophene led to generally high overall yields for the construction of heterocyclic triads. C-H bond activation provided an efficient strategy for the Pd-catalyzed cross-coupling at C(2) of oxazoles. Further analog variation was achieved with a copper-catalyzed azide-alkyne cycloaddition to form a 1,4-substituted 1,2,3-triazole. Potency and selectivity of the final hydroxymethyl products were determined in the NCI-60 cell assay. Two lead compounds were tested in vivo and compared to NSC 652287. The evaluation of these compounds continues with a thermal shift assay coupled with differential mass spectrometry for biological target identification. The chemical stability of select triads are also discussed.
The second chapter details the synthesis of thienopyridone and thienopyrimidine dione analogs as inhibitors of protein tyrosine phosphatase 4A3 (PTP4A3), an attractive anticancer target. Derivatization by photooxygenation led to a compound with a unique structural motif, high potency, and excellent selectivity towards PTP4A3. An automated synthesis strategy using Lilly’s Automated Synthesis Lab was employed for analog synthesis.

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  • Heterocyclic Chemistry at The Scripps Research Institute

    Nitrogen heterocycles represent vital structural motifs in biologically-active natural products and pharmaceuticals

  • Essentials of Heterocyclic Chemistry IV; ..

    Heterocyclic Aromatic Compounds | Heterocyclic …

  • Synthesis of Lactones and Other Heterocycles | …

    In organic chemistry, cyclic compounds that contain at least one ring atom that is not a carbon are called heterocycles

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Use in the Synthesis of Non-heterocycles — Johns …

Key product strengths include fluorinated compounds, boronic acids, heterocycles, chiral compounds, and acyl and sulphonyl halides. Lancaster Synthesis has exclusive distribution arrangements with many of its suppliers, making it the only laboratory scale commercial source of many compounds.

Use in the Synthesis of Non-heterocycles

Saturated N-heterocycles are prevalent in biologically active molecules and are increasingly attractive scaffolds in the development of new pharmaceuticals. Unlike their aromatic counterparts, there are limited strategies for facile construction of substituted saturated N-heterocycles by convergent, predictable methods. In this Synopsis, we discuss recent advances in the synthesis of these compounds, focusing on approaches that offer generality and convenience from widely available building blocks.

Comprehensive Heterocyclic Chemistry

Scott E. Allen was born in 1984 in Kutztown, Pennsylvania. He received his B.S. in chemistry from Penn State University, where he performed undergraduate research with Dr. Xumu Zhang. He then joined the laboratory of Dr. Marisa C. Kozlowski at the University of Pennsylvania, where his research focused on computational organic chemistry studies of N-heterocyclic carbene-catalyzed reactions in collaboration with Dr. Jeffery Bode at the ETH. Upon completion of his Ph.D. in early 2013, Scott joined the laboratory of Dr. Albert Bowers at the UNC Eshelman School of Pharmacy as a postdoctoral associate.

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