Evaluation of 3-carbamoylpropanoic acid analogs as inhibitors of human hypoxia-inducible factor (HIF) prolyl hydroxylase domain enzymes
There is current interest in developing human hypoxia-inducible factor (HIF) prolyl hydroxylase domain (PHD) inhibitors for the treatment of anemia and other hypoxia-related diseases. We describe the synthesis of 3-carbamoylpropanoic acid derivatives and their evaluation as human PHD-2 inhibitors. M...
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| Published in | Medicinal chemistry research Vol. 30; no. 4; pp. 977 - 986 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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01.04.2021
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| Abstract | There is current interest in developing human hypoxia-inducible factor (HIF) prolyl hydroxylase domain (PHD) inhibitors for the treatment of anemia and other hypoxia-related diseases. We describe the synthesis of 3-carbamoylpropanoic acid derivatives and their evaluation as human PHD-2 inhibitors. MS assays indicated that derivatives with a 3-carbamoylpropanoic acids-containing benzoxazole moiety are inhibitors of PHD-2 with IC
50
values of 2.24 μM and 1.32 μM, respectively. However, neither the acids nor their respective ethyl esters were observed to upregulate HIF-1α levels in cells. |
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| AbstractList | There is current interest in developing human hypoxia-inducible factor (HIF) prolyl hydroxylase domain (PHD) inhibitors for the treatment of anemia and other hypoxia-related diseases. We describe the synthesis of 3-carbamoylpropanoic acid derivatives and their evaluation as human PHD-2 inhibitors. MS assays indicated that derivatives with a 3-carbamoylpropanoic acids-containing benzoxazole moiety are inhibitors of PHD-2 with IC
50
values of 2.24 μM and 1.32 μM, respectively. However, neither the acids nor their respective ethyl esters were observed to upregulate HIF-1α levels in cells. There is current interest in developing human hypoxia-inducible factor (HIF) prolyl hydroxylase domain (PHD) inhibitors for the treatment of anemia and other hypoxia-related diseases. We describe the synthesis of 3-carbamoylpropanoic acid derivatives and their evaluation as human PHD-2 inhibitors. MS assays indicated that derivatives with a 3-carbamoylpropanoic acids-containing benzoxazole moiety are inhibitors of PHD-2 with IC50 values of 2.24 μM and 1.32 μM, respectively. However, neither the acids nor their respective ethyl esters were observed to upregulate HIF-1α levels in cells. |
| Author | Abboud, Martine I. Chan, YanYing Yeoh, KarKheng Toh, LeeRoy Schofield, Christopher J. Chong, MuiPhin Tumber, Anthony Chan, MunChiang |
| Author_xml | – sequence: 1 givenname: MuiPhin surname: Chong fullname: Chong, MuiPhin organization: School of Chemical Sciences, Universiti Sains Malaysia – sequence: 2 givenname: LeeRoy surname: Toh fullname: Toh, LeeRoy organization: School of Chemical Sciences, Universiti Sains Malaysia – sequence: 3 givenname: Anthony surname: Tumber fullname: Tumber, Anthony organization: Chemical Research Laboratory, University of Oxford – sequence: 4 givenname: YanYing surname: Chan fullname: Chan, YanYing organization: Department of Molecular Medicine, University of Malaya – sequence: 5 givenname: MunChiang surname: Chan fullname: Chan, MunChiang organization: Department of Molecular Medicine, University of Malaya – sequence: 6 givenname: Martine I. surname: Abboud fullname: Abboud, Martine I. organization: Chemical Research Laboratory, University of Oxford – sequence: 7 givenname: Christopher J. surname: Schofield fullname: Schofield, Christopher J. organization: Chemical Research Laboratory, University of Oxford – sequence: 8 givenname: KarKheng orcidid: 0000-0002-3072-0426 surname: Yeoh fullname: Yeoh, KarKheng email: kkyeoh@usm.my organization: School of Chemical Sciences, Universiti Sains Malaysia |
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| Cites_doi | 10.1038/20459 10.1038/nrc2540 10.1074/jbc.M002740200 10.1136/heartjnl-2014-306118.74 10.1016/j.critrevonc.2005.12.003 10.1513/AnnalsATS.201403-108AW 10.1016/j.bbrc.2005.08.193 10.1038/s41374-019-0239-4 10.1039/C7SC02103H 10.1038/nrneph.2015.193 10.1371/journal.pone.0216134 10.1073/pnas.0601283103 10.1007/s40265-019-01077-1 10.1021/pr100269b 10.1056/NEJMoa1813599 10.1039/c0cs00203h 10.1371/journal.pone.0132004 10.1007/978-0-387-75246-4_97 10.1074/jbc.M608337200 10.2215/CJN.06890615 10.1101/gad.1145503 10.1002/cmdc.201600012 10.1016/j.kint.2019.02.016 10.1039/C8CC00387D 10.1146/annurev-biochem-061516-044724 10.1038/ncomms12673 10.1517/13543776.2010.510836 10.1159/000496531 10.1021/ol8020989 10.1002/cbic.201800246 10.1016/j.mam.2016.01.001 10.1053/j.ajkd.2016.12.011 10.1002/ejoc.200300620 10.1016/S0092-8674(01)00507-4 10.1002/cmdc.201900557 10.1186/rr27 10.1523/JNEUROSCI.22-20-08922.2002 10.1074/jbc.M116.749291 10.1074/jbc.M204619200 10.1039/C2OB26648B 10.1073/pnas.1523005113 10.1124/jpet.117.242503 10.3109/15376516.2012.673088 10.1016/j.neuropharm.2018.12.021 |
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| Keywords | Hypoxia-inducible factor 3-carbamoylpropanoic acid derivatives PHD inhibitors HIF Prolyl hydroxylase domain 2-oxoglutarate/alpha-ketoglutarate dependent oxygenase |
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| SubjectTerms | Acids Anemia Biochemistry Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Domains Esters Ethyl esters Hydroxylase Hypoxia Hypoxia-inducible factor 1a Inhibitors Inorganic Chemistry Medicinal Chemistry Original Research Pharmacology/Toxicology Prolyl hydroxylase |
| Title | Evaluation of 3-carbamoylpropanoic acid analogs as inhibitors of human hypoxia-inducible factor (HIF) prolyl hydroxylase domain enzymes |
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