(Pd/C-mediated)coupling–iodocyclization–coupling strategy in discovery of novel PDE4 inhibitors: a new synthesis of pyrazolopyrimidines

P. Mahesh Kumar; K. Siva Kumar; Chandana L. T. Meda; G. Rajeshwar Reddy; Pradeep K. Mohakhud; K. Mukkanti; G. Rama Krishna; C. Malla Reddy; D. Rambabu; K. Shiva Kumar; K. Krishna Priya; Keerthana Sarma Chennubhotla; Rakesh Kumar Banote; Pushkar Kulkarni; Kishore V. L. Parsa; Manojit Pal

doi:10.1039/C2MD00273F

(Pd/C-mediated)coupling–iodocyclization–coupling strategy in discovery of novel PDE4 inhibitors: a new synthesis of pyrazolopyrimidines†

P. Mahesh Kumar,^ab K. Siva Kumar,^a Chandana L. T. Meda,^c G. Rajeshwar Reddy,^a Pradeep K. Mohakhud,^a K. Mukkanti,^b G. Rama Krishna,^d C. Malla Reddy,^d D. Rambabu,^c K. Shiva Kumar,^c K. Krishna Priya,^c Keerthana Sarma Chennubhotla,^e Rakesh Kumar Banote,^e Pushkar Kulkarni,^e Kishore V. L. Parsa*^c and Manojit Pal*^c

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* Corresponding authors

^a Custom Pharmaceutical Services, Dr Reddy's Laboratories Limited, Bollaram Road Miyapur, Hyderabad 500 049, India

^b Chemistry Division, Institute of Science and Technology, Jawaharlal Nehru Technological University, Hyderabad 500089, Andhra Pradesh, India

^c Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, Andhra Pradesh, India
E-mail: KishoreP@ilsresearch.org, manojitpal@rediffmail.com

^d Department of Chemical Sciences, Indian Institute of Science and Research, Kolkata, West Bengal, India

^e Zephase Therapeutics Pvt. Ltd (An incubated company at the Institute of Life Sciences), University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, Andhra Pradesh, India

Abstract

Pyranones fused with a pyrazolopyrimidine moiety were prepared via regioselective construction of pyranone ring using (Pd/C-mediated)coupling–iodocyclization followed by Sonogashira/Heck/Suzuki reactions. The pyrazolopyrimidine based reactant required was obtained via a new H₃PO₃ mediated condensation reaction. This strategy has led to the discovery of a novel and potentially safe PDE4 inhibitor.

MedChemComm

(Pd/C-mediated)coupling–iodocyclization–coupling strategy in discovery of novel PDE4 inhibitors: a new synthesis of pyrazolopyrimidines†

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