scholarly journals Late-Stage Diversification of Biologically Active Molecules via Chemoenzymatic C–H Functionalization

ACS Catalysis ◽  
2016 ◽  
Vol 6 (3) ◽  
pp. 1451-1454 ◽  
Author(s):  
Landon J. Durak ◽  
James T. Payne ◽  
Jared C. Lewis
Keyword(s):  
Late Stage ◽  
Biologically Active

scholarly journals Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Masakazu Nambo ◽  
Jacky C.-H. Yim ◽  
Luiza B. O. Freitas ◽  
Yasuyo Tahara ◽  
Zachary T. Ariki ◽  
...  
Keyword(s):  
Biological Activity ◽  
Late Stage ◽  
Recent Progress ◽  
Cross Coupling ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Arylboronic Acids ◽  
Modular Synthesis ◽  
Synthetic Routes

Abstract α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting in improved biological activity and stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes are still rare. Herein we describe the Pd-catalyzed Suzuki-Miyaura cross-coupling of α-fluorinated benzylic triflones with arylboronic acids affording structurally diverse α-fluorinated diarylmethanes. The ease of synthesis of fluorinated triflones as the key starting materials enables powerful late-stage transformations of known biologically active compounds into fluorinated analogs.

Synthetic approaches to [5,6]-benzannulated spiroketal natural products

2011 ◽  
Vol 84 (6) ◽  
pp. 1379-1390 ◽  
Author(s):  
Michael C. McLeod ◽  
Margaret A. Brimble ◽  
Dominea C. K. Rathwell ◽  
Zoe E. Wilson ◽  
Tsz-Ying Yuen
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Electronic Properties ◽  
Late Stage ◽  
Biologically Active ◽  
Formal Synthesis ◽  
Berkelic Acid ◽  
Synthetic Approaches

Studies toward the synthesis of three biologically active [5,6]-benzannulated spiroketal natural products are described. The first total synthesis of paecilospirone is reported, employing a late-stage, pH-neutral spiroketalization. A formal synthesis of γ-rubromycin is described, where the spiroketal moiety is formed by delicate manipulation of the electronic properties of the spirocyclization precursor. Finally, model work toward the total synthesis of berkelic acid is summarized, introducing a novel Horner–Wadsworth–Emmons/oxa-Michael (HWE/oxa-M) cascade to access the spiroketal precursor.

scholarly journals Photooxygenation of an amino-thienopyridone yields a more potent PTP4A3 inhibitor

2016 ◽  
Vol 14 (27) ◽  
pp. 6398-6402 ◽  
Author(s):  
Joseph M. Salamoun ◽  
Kelley E. McQueeney ◽  
Kalyani Patil ◽  
Steven J. Geib ◽  
Elizabeth R. Sharlow ◽  
...  
Keyword(s):  
Late Stage ◽  
Biologically Active

Late-stage photooxygenation can generate novel biologically active lead structures.

Late-stage diversification of biologically active pyridazinones via a direct C–H functionalization strategy

2015 ◽  
Vol 13 (2) ◽  
pp. 539-548 ◽  
Author(s):  
Wei Li ◽  
Zhoulong Fan ◽  
Kaijun Geng ◽  
Youjun Xu ◽  
Ao Zhang
Keyword(s):  
Late Stage ◽  
Biologically Active ◽  
Directing Group

Divergent ortho-selective C–H functionalization was successfully established using a pyridazinone moiety as an internal directing group.

scholarly journals Late stage iodination of biologically active agents using a one-pot process from aryl amines

RSC Advances ◽  
2017 ◽  
Vol 7 (86) ◽  
pp. 54881-54891 ◽  
Author(s):  
Nikki L. Sloan ◽  
Sajinder K. Luthra ◽  
Graeme McRobbie ◽  
Sally L. Pimlott ◽  
Andrew Sutherland
Keyword(s):  
Late Stage ◽  
Biologically Active ◽  
One Pot ◽  
Aryl Iodide ◽  
Aryl Amines ◽  
Tandem Process

A tandem process has been developed for the general preparation of aryl iodide compounds from anilines that is also applicable for the late-stage iodination of biologically active agents.

scholarly journals Fluorination methods in drug discovery

2016 ◽  
Vol 14 (36) ◽  
pp. 8398-8427 ◽  
Author(s):  
Damian E. Yerien ◽  
Sergio Bonesi ◽  
Al Postigo
Keyword(s):  
Drug Discovery ◽  
Pharmaceutical Industry ◽  
Late Stage ◽  
Biologically Active ◽  
Metabolic Degradation

Late stage fluorination methods applied to biologically-active drugs have provided the pharmaceutical industry with new leads that show improved properties such as modulation of lipophilicity, electronegativity, basicity, bioavailability, and deceleration of metabolic degradation.

Late-Stage Functionalization of Biologically Active Heterocycles Through Photoredox Catalysis

2014 ◽  
Vol 126 (19) ◽  
pp. 4902-4906 ◽  
Author(s):  
Daniel A. DiRocco ◽  
Kevin Dykstra ◽  
Shane Krska ◽  
Petr Vachal ◽  
Donald V. Conway ◽  
...  
Keyword(s):  
Late Stage ◽  
Biologically Active ◽  
Photoredox Catalysis

General and selective syn-carboxylation-trifluoromethylation of terminal alkynes: application to the late-stage modification of dehydrocholic acid

2019 ◽  
Vol 55 (28) ◽  
pp. 4099-4102 ◽  
Author(s):  
Song-Lin Zhang ◽  
Chang Xiao ◽  
Hai-Xing Wan ◽  
Xiaoming Zhang
Keyword(s):  
Late Stage ◽  
Triple Bond ◽  
Biologically Active ◽  
Terminal Alkynes ◽  
Dehydrocholic Acid ◽  
Enol Esters

A general and selective syn-carboxylation-trifluoromethylation across the triple bond of terminal alkynes is developed by virtue of a reactive Cu(iii)–CF3 complex, which produces a broad range of biologically active trifluoromethylated enol esters with excellent regio- and stereoselectivity.

Late-Stage Functionalization of Biologically Active Heterocycles Through Photoredox Catalysis

2014 ◽  
Vol 53 (19) ◽  
pp. 4802-4806 ◽  
Author(s):  
Daniel A. DiRocco ◽  
Kevin Dykstra ◽  
Shane Krska ◽  
Petr Vachal ◽  
Donald V. Conway ◽  
...  
Keyword(s):  
Late Stage ◽  
Biologically Active ◽  
Photoredox Catalysis

scholarly journals One-pot ortho-amination of aryl C–H bonds using consecutive iron and copper catalysis

2019 ◽  
Vol 17 (18) ◽  
pp. 4629-4639 ◽  
Author(s):  
Martyn C. Henry ◽  
Rochelle McGrory ◽  
Réka J. Faggyas ◽  
Mohamed A. B. Mostafa ◽  
Andrew Sutherland
Keyword(s):  
Late Stage ◽  
Biologically Active ◽  
Copper Catalysis ◽  
One Pot ◽  
Structural Diversification

A one-pot ortho-amination of activated arenes using sequential iron and copper catalysis has been developed and utilised for the late-stage structural diversification of biologically active 3,4-dihydroquinolin-2-ones.

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