- Continuous flow synthesis of thieno[2,3-c ]isoquinolin-5(4 H)-one scaffold: A valuable source of PARP-1 inhibitors
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An efficient multistep method for the continuous flow synthesis of thieno[2,3-c]isoquinolin-5(4H)-one-A (TIQ-A), an important pharmacological tool and building block for PARP-1 inhibitors, has been developed. The synthesis involves a Suzuki coupling reaction to generate 3-phenylthiophene-2-carboxylic acid which is transformed into the corresponding acyl azide and readily cyclized by a thermal Curtius rearrangement. A statistical design of experiments (DoE) was employed as a valuable support for decision-making of further experiments enabling the development of a robust and reliable protocol for large-scale preparation. As a result, the reactions are facile, safe, and easy to scale-up. The large-scale applicability of this improved flow method was tested by conducting the reactions on multigram scale to produce the desired product in high yield and quality for biopharmacological appraisals.
- Filipponi, Paolo,Ostacolo, Carmine,Novellino, Ettore,Pellicciari, Roberto,Gioiello, Antimo
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p. 1345 - 1353
(2015/02/19)
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- Thieno[2,3-c]iosquinolines for use as inhibitors of parp
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Heterocyclic derivatives, including derivatives of thieno[2,3-c]isoquinolin-3-one and their use in therapy as inhibitors of poly(ADP-ribose) polymers (PARP), for use in the prevention and treatment of tissue damage due to ischaemia and reperfusion, degene
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- Towards new neuroprotective agents: Design and synthesis of 4H-thieno[2,3-c] isoquinolin-5-one derivatives as potent PARP-1 inhibitors
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An excessive activation of poly(ADP-ribose) polymerase-1 (PARP-1), a nuclear enzyme able to catalyze the transfer of ADP-ribose from NAD to acceptor proteins, is involved in the progression of neuronal damage after brain insult. Potent and selective PARP-
- Pellicciari, Roberto,Camaioni, Emidio,Costantino, Gabriele,Marinozzi, Maura,Macchiarulo, Antonio,Moroni, Flavio,Natalini, Benedetto
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p. 851 - 858
(2007/10/03)
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