Identification and synthesis of 2,7-diamino-thiazolo[5,4- d]pyrimidine derivatives as TRPV1 antagonists
The identification and synthesis of 2,7-diamino-thiazolo[5,4- d]pyrimidines as TRPV1 antagonists is described. An exploration of the structure–activity relationships at the 2-, 5-, and 7-positions of the thiazolo[5,4- d]pyrimidine led to the identification of several highly potent TRPV1 antagonists,...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 19; no. 1; pp. 40 - 46 |
|---|---|
| Main Authors | , , , , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Amsterdam
Elsevier Ltd
2009
Elsevier |
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| Abstract | The identification and synthesis of 2,7-diamino-thiazolo[5,4-
d]pyrimidines as TRPV1 antagonists is described. An exploration of the structure–activity relationships at the 2-, 5-, and 7-positions of the thiazolo[5,4-
d]pyrimidine led to the identification of several highly potent TRPV1 antagonists, including
3. Compound
3 was orally bioavailable and afforded a significant reversal of carrageenan-induced thermal hyperalgesia.
We have identified and synthesized a series of 2,7-diamino-thiazolo[5,4-
d]pyrimidines as TRPV1 antagonists. An exploration of the structure–activity relationships at the 2-, 5-, and 7-positions of the thiazolo[5,4-
d]pyrimidine led to the identification of several potent TRPV1 antagonists, including
3,
29,
51, and
57. Compound
3 was orally bioavailable and afforded a significant reversal of carrageenan-induced thermal hyperalgesia with an ED
50
=
0.5
mg/kg in rats. |
|---|---|
| AbstractList | The identification and synthesis of 2,7-diamino-thiazolo[5,4-
d]pyrimidines as TRPV1 antagonists is described. An exploration of the structure–activity relationships at the 2-, 5-, and 7-positions of the thiazolo[5,4-
d]pyrimidine led to the identification of several highly potent TRPV1 antagonists, including
3. Compound
3 was orally bioavailable and afforded a significant reversal of carrageenan-induced thermal hyperalgesia.
We have identified and synthesized a series of 2,7-diamino-thiazolo[5,4-
d]pyrimidines as TRPV1 antagonists. An exploration of the structure–activity relationships at the 2-, 5-, and 7-positions of the thiazolo[5,4-
d]pyrimidine led to the identification of several potent TRPV1 antagonists, including
3,
29,
51, and
57. Compound
3 was orally bioavailable and afforded a significant reversal of carrageenan-induced thermal hyperalgesia with an ED
50
=
0.5
mg/kg in rats. We have identified and synthesized a series of 2,7-diamino-thiazolo[5,4-d]pyrimidines as TRPV1 antagonists. An exploration of the structure-activity relationships at the 2-, 5-, and 7-positions of the thiazolo[5,4-d]pyrimidine led to the identification of several potent TRPV1 antagonists, including 3, 29, 51, and 57. Compound 3 was orally bioavailable and afforded a significant reversal of carrageenan-induced thermal hyperalgesia with an ED50 = 0.5 mg/kg in rats. We have identified and synthesized a series of 2,7-diamino-thiazolo[5,4-d]pyrimidines as TRPV1 antagonists. An exploration of the structure-activity relationships at the 2-, 5-, and 7-positions of the thiazolo[5,4-d]pyrimidine led to the identification of several potent TRPV1 antagonists, including 3, 29, 51, and 57. Compound 3 was orally bioavailable and afforded a significant reversal of carrageenan-induced thermal hyperalgesia with an ED(50)=0.5mg/kg in rats. We have identified and synthesized a series of 2,7-diamino-thiazolo[5,4- d]pyrimidines as TRPV1 antagonists. An exploration of the structure- activity relationships at the 2-, 5-, and 7-positions of the thiazolo[5,4- d]pyrimidine led to the identification of several potent TRPV1 antagonists, including 3, 29, 51, and 57. Compound 3 was orally bioavailable and afforded a significant reversal of carrageenan-induced thermal hyperalgesia with an ED sub(50) = 0.5 mg/kg in rats. |
| Author | Kansagara, Mena Scott, Brian P. Hack, Michael D. Bhattacharya, Anindya Maher, Michael P. Rynberg, Raymond Xiao, Wei Guy Breitenbucher, J. Luo, Lin Rizzolio, Michele Peterson, Matthew L. Chaplan, Sandra R. Lebsack, Alec D. Nasser, Nadia Ao, Hong Branstetter, Bryan J. Wickenden, Alan D. |
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| Cites_doi | 10.1016/j.bmcl.2005.08.100 10.1126/science.288.5464.306 10.1038/39807 10.1016/S1097-2765(02)00448-3 10.1021/jo0517702 10.1038/35012076 10.1021/jm060637e 10.1016/S0165-6147(02)01999-5 10.1021/ol0200091 10.1016/S0065-7743(05)40012-3 10.1517/13543776.18.2.159 10.1124/jpet.107.127258 10.1146/annurev.neuro.24.1.487 10.1517/13543776.13.12.1825 |
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| Keywords | Antagonists TRPV1 Thiazolo-pyrimidine Rat Rodentia Oral administration Bioavailability In vitro In vivo Vertebrata VR1 vanilloid receptor TRPV1 vanilloid receptor Mammalia Analgesic TRP ion channel Structure activity relation Animal Chlorine Organic compounds Antagonist Fluorine Organic compounds Pharmacokinetics Chemical synthesis |
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| Snippet | The identification and synthesis of 2,7-diamino-thiazolo[5,4-
d]pyrimidines as TRPV1 antagonists is described. An exploration of the structure–activity... We have identified and synthesized a series of 2,7-diamino-thiazolo[5,4-d]pyrimidines as TRPV1 antagonists. An exploration of the structure-activity... We have identified and synthesized a series of 2,7-diamino-thiazolo[5,4- d]pyrimidines as TRPV1 antagonists. An exploration of the structure- activity... |
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| SubjectTerms | Administration, Oral Analgesics Animals Antagonists Biological and medical sciences Hyperalgesia - chemically induced Hyperalgesia - drug therapy Medical sciences Neuropharmacology Pharmacology. Drug treatments Pyrimidines - chemical synthesis Pyrimidines - pharmacology Rats Structure-Activity Relationship Thiazoles Thiazolo-pyrimidine Treatment Outcome TRPV Cation Channels - antagonists & inhibitors TRPV1 |
| Title | Identification and synthesis of 2,7-diamino-thiazolo[5,4- d]pyrimidine derivatives as TRPV1 antagonists |
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