Discovery of N-[2-[2-[[3-Methoxy-4-(5-oxazolyl)phenyl]amino]-5-oxazolyl]phenyl]-N-methyl-4- morpholineacetamide as a Novel and Potent Inhibitor of Inosine Monophosphate Dehydrogenase with Excellent in Vivo Activity
Inosine monophosphate dehydrogenase (IMPDH) is a key enzyme that is involved in the de novo synthesis of purine nucleotides. Novel 2-aminooxazoles were synthesized and tested for inhibition of IMPDH catalytic activity. Multiple analogues based on this chemotype were found to inhibit IMPDH with low n...
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| Veröffentlicht in: | Journal of medicinal chemistry 2002-05, Vol.45 (11), p.2127-2130 |
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| container_title | Journal of medicinal chemistry |
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| creator | Dhar, T. G. Murali Shen, Zhongqi Guo, Junqing Liu, Chunjian Watterson, Scott H Gu, Henry H Pitts, William J Fleener, Catherine A Rouleau, Katherine A Sherbina, N. Z McIntyre, Kim W Witmer, Mark R Tredup, Jeffrey A Chen, Bang-Chi Zhao, Rulin Bednarz, Mark S Cheney, Daniel L MacMaster, John F Miller, Laura M Berry, Karen K Harper, Timothy W Barrish, Joel C Hollenbaugh, Diane L Iwanowicz, Edwin J |
| description | Inosine monophosphate dehydrogenase (IMPDH) is a key enzyme that is involved in the de novo synthesis of purine nucleotides. Novel 2-aminooxazoles were synthesized and tested for inhibition of IMPDH catalytic activity. Multiple analogues based on this chemotype were found to inhibit IMPDH with low nanomolar potency. One of the analogues (compound 23) showed excellent in vivo activity in the inhibition of antibody production in mice and in the adjuvant induced arthritis model in rats. |
| doi_str_mv | 10.1021/jm0105777 |
| format | Article |
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G. Murali ; Shen, Zhongqi ; Guo, Junqing ; Liu, Chunjian ; Watterson, Scott H ; Gu, Henry H ; Pitts, William J ; Fleener, Catherine A ; Rouleau, Katherine A ; Sherbina, N. Z ; McIntyre, Kim W ; Witmer, Mark R ; Tredup, Jeffrey A ; Chen, Bang-Chi ; Zhao, Rulin ; Bednarz, Mark S ; Cheney, Daniel L ; MacMaster, John F ; Miller, Laura M ; Berry, Karen K ; Harper, Timothy W ; Barrish, Joel C ; Hollenbaugh, Diane L ; Iwanowicz, Edwin J</creator><creatorcontrib>Dhar, T. G. Murali ; Shen, Zhongqi ; Guo, Junqing ; Liu, Chunjian ; Watterson, Scott H ; Gu, Henry H ; Pitts, William J ; Fleener, Catherine A ; Rouleau, Katherine A ; Sherbina, N. Z ; McIntyre, Kim W ; Witmer, Mark R ; Tredup, Jeffrey A ; Chen, Bang-Chi ; Zhao, Rulin ; Bednarz, Mark S ; Cheney, Daniel L ; MacMaster, John F ; Miller, Laura M ; Berry, Karen K ; Harper, Timothy W ; Barrish, Joel C ; Hollenbaugh, Diane L ; Iwanowicz, Edwin J</creatorcontrib><description>Inosine monophosphate dehydrogenase (IMPDH) is a key enzyme that is involved in the de novo synthesis of purine nucleotides. Novel 2-aminooxazoles were synthesized and tested for inhibition of IMPDH catalytic activity. Multiple analogues based on this chemotype were found to inhibit IMPDH with low nanomolar potency. One of the analogues (compound 23) showed excellent in vivo activity in the inhibition of antibody production in mice and in the adjuvant induced arthritis model in rats.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm0105777</identifier><identifier>PMID: 12014950</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Antibody Formation - drug effects ; Arthritis, Experimental - drug therapy ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Enzyme-Linked Immunosorbent Assay ; Immunomodulators ; IMP Dehydrogenase - antagonists & inhibitors ; Male ; Medical sciences ; Mice ; Mice, Inbred BALB C ; Morpholines - chemical synthesis ; Morpholines - chemistry ; Morpholines - pharmacology ; Mycophenolic Acid - analogs & derivatives ; Mycophenolic Acid - pharmacology ; Oxazoles - chemical synthesis ; Oxazoles - chemistry ; Oxazoles - pharmacology ; Pharmacology. 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G. Murali</creatorcontrib><creatorcontrib>Shen, Zhongqi</creatorcontrib><creatorcontrib>Guo, Junqing</creatorcontrib><creatorcontrib>Liu, Chunjian</creatorcontrib><creatorcontrib>Watterson, Scott H</creatorcontrib><creatorcontrib>Gu, Henry H</creatorcontrib><creatorcontrib>Pitts, William J</creatorcontrib><creatorcontrib>Fleener, Catherine A</creatorcontrib><creatorcontrib>Rouleau, Katherine A</creatorcontrib><creatorcontrib>Sherbina, N. Z</creatorcontrib><creatorcontrib>McIntyre, Kim W</creatorcontrib><creatorcontrib>Witmer, Mark R</creatorcontrib><creatorcontrib>Tredup, Jeffrey A</creatorcontrib><creatorcontrib>Chen, Bang-Chi</creatorcontrib><creatorcontrib>Zhao, Rulin</creatorcontrib><creatorcontrib>Bednarz, Mark S</creatorcontrib><creatorcontrib>Cheney, Daniel L</creatorcontrib><creatorcontrib>MacMaster, John F</creatorcontrib><creatorcontrib>Miller, Laura M</creatorcontrib><creatorcontrib>Berry, Karen K</creatorcontrib><creatorcontrib>Harper, Timothy W</creatorcontrib><creatorcontrib>Barrish, Joel C</creatorcontrib><creatorcontrib>Hollenbaugh, Diane L</creatorcontrib><creatorcontrib>Iwanowicz, Edwin J</creatorcontrib><title>Discovery of N-[2-[2-[[3-Methoxy-4-(5-oxazolyl)phenyl]amino]-5-oxazolyl]phenyl]-N-methyl-4- morpholineacetamide as a Novel and Potent Inhibitor of Inosine Monophosphate Dehydrogenase with Excellent in Vivo Activity</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Inosine monophosphate dehydrogenase (IMPDH) is a key enzyme that is involved in the de novo synthesis of purine nucleotides. Novel 2-aminooxazoles were synthesized and tested for inhibition of IMPDH catalytic activity. Multiple analogues based on this chemotype were found to inhibit IMPDH with low nanomolar potency. One of the analogues (compound 23) showed excellent in vivo activity in the inhibition of antibody production in mice and in the adjuvant induced arthritis model in rats.</description><subject>Animals</subject><subject>Antibody Formation - drug effects</subject><subject>Arthritis, Experimental - drug therapy</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Enzyme-Linked Immunosorbent Assay</subject><subject>Immunomodulators</subject><subject>IMP Dehydrogenase - antagonists & inhibitors</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Mice, Inbred BALB C</subject><subject>Morpholines - chemical synthesis</subject><subject>Morpholines - chemistry</subject><subject>Morpholines - pharmacology</subject><subject>Mycophenolic Acid - analogs & derivatives</subject><subject>Mycophenolic Acid - pharmacology</subject><subject>Oxazoles - chemical synthesis</subject><subject>Oxazoles - chemistry</subject><subject>Oxazoles - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Rats</subject><subject>Rats, Inbred Lew</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1uEzEUhUcIRENhwQsgb0B0YbA9P55ZVk1bgtIQqQUWVWR5Zu4wTmfsYDshw4PyPDgkajZIlu7ifOf46twoek3JB0oY_bjsCSUp5_xJNKIpIzjJSfI0GhHCGGYZi0-iF84tCSExZfHz6IQyQpMiJaPoz1i5ymzADsg0aIbv2b93H-Mb8K3ZDjjB71NstvK36YbubNWCHrqF7JU2C3wUFgcBz3AfjEMXfKg3dtWaTmmQFfjgqQFJhySahR87JHWN5saD9miiW1Uqb-xui4k2LnjQjdEm-N2qlR7QGNqhtuYHaOkA_VK-RZfbCrpu51cafVMbg84rrzbKDy-jZ43sHLw6zNPo69Xl3cUnPP1yPbk4n2IZU-oxUN6QTJY5FISFJqEo8tCRzHiZFySroKplyXOWJRSauM44z3PWlJwAy9OshPg0erfPXVnzcw3Oiz70GZaSGszaCU6zgtGEB_BsD1bWOGehESuremkHQYnYHVE8HjGwbw6h67KH-kgerhaAtwdAukp2jZW6Uu7IxRmnBYkDh_ecch62j7q0DyLjMU_F3fxWfL6-nU2_X83F-JgrKyeWZm116O4_C_4FFNPB6w</recordid><startdate>20020523</startdate><enddate>20020523</enddate><creator>Dhar, T. G. Murali</creator><creator>Shen, Zhongqi</creator><creator>Guo, Junqing</creator><creator>Liu, Chunjian</creator><creator>Watterson, Scott H</creator><creator>Gu, Henry H</creator><creator>Pitts, William J</creator><creator>Fleener, Catherine A</creator><creator>Rouleau, Katherine A</creator><creator>Sherbina, N. Z</creator><creator>McIntyre, Kim W</creator><creator>Witmer, Mark R</creator><creator>Tredup, Jeffrey A</creator><creator>Chen, Bang-Chi</creator><creator>Zhao, Rulin</creator><creator>Bednarz, Mark S</creator><creator>Cheney, Daniel L</creator><creator>MacMaster, John F</creator><creator>Miller, Laura M</creator><creator>Berry, Karen K</creator><creator>Harper, Timothy W</creator><creator>Barrish, Joel C</creator><creator>Hollenbaugh, Diane L</creator><creator>Iwanowicz, Edwin J</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20020523</creationdate><title>Discovery of N-[2-[2-[[3-Methoxy-4-(5-oxazolyl)phenyl]amino]-5-oxazolyl]phenyl]-N-methyl-4- morpholineacetamide as a Novel and Potent Inhibitor of Inosine Monophosphate Dehydrogenase with Excellent in Vivo Activity</title><author>Dhar, T. G. Murali ; Shen, Zhongqi ; Guo, Junqing ; Liu, Chunjian ; Watterson, Scott H ; Gu, Henry H ; Pitts, William J ; Fleener, Catherine A ; Rouleau, Katherine A ; Sherbina, N. Z ; McIntyre, Kim W ; Witmer, Mark R ; Tredup, Jeffrey A ; Chen, Bang-Chi ; Zhao, Rulin ; Bednarz, Mark S ; Cheney, Daniel L ; MacMaster, John F ; Miller, Laura M ; Berry, Karen K ; Harper, Timothy W ; Barrish, Joel C ; Hollenbaugh, Diane L ; Iwanowicz, Edwin J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a311t-e17f06ab8e902021e998031a67b8906cecdab782641ef3d677882fb70e2856be3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Animals</topic><topic>Antibody Formation - drug effects</topic><topic>Arthritis, Experimental - drug therapy</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Enzyme-Linked Immunosorbent Assay</topic><topic>Immunomodulators</topic><topic>IMP Dehydrogenase - antagonists & inhibitors</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Mice, Inbred BALB C</topic><topic>Morpholines - chemical synthesis</topic><topic>Morpholines - chemistry</topic><topic>Morpholines - pharmacology</topic><topic>Mycophenolic Acid - analogs & derivatives</topic><topic>Mycophenolic Acid - pharmacology</topic><topic>Oxazoles - chemical synthesis</topic><topic>Oxazoles - chemistry</topic><topic>Oxazoles - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Rats</topic><topic>Rats, Inbred Lew</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dhar, T. G. Murali</creatorcontrib><creatorcontrib>Shen, Zhongqi</creatorcontrib><creatorcontrib>Guo, Junqing</creatorcontrib><creatorcontrib>Liu, Chunjian</creatorcontrib><creatorcontrib>Watterson, Scott H</creatorcontrib><creatorcontrib>Gu, Henry H</creatorcontrib><creatorcontrib>Pitts, William J</creatorcontrib><creatorcontrib>Fleener, Catherine A</creatorcontrib><creatorcontrib>Rouleau, Katherine A</creatorcontrib><creatorcontrib>Sherbina, N. 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G. Murali</au><au>Shen, Zhongqi</au><au>Guo, Junqing</au><au>Liu, Chunjian</au><au>Watterson, Scott H</au><au>Gu, Henry H</au><au>Pitts, William J</au><au>Fleener, Catherine A</au><au>Rouleau, Katherine A</au><au>Sherbina, N. Z</au><au>McIntyre, Kim W</au><au>Witmer, Mark R</au><au>Tredup, Jeffrey A</au><au>Chen, Bang-Chi</au><au>Zhao, Rulin</au><au>Bednarz, Mark S</au><au>Cheney, Daniel L</au><au>MacMaster, John F</au><au>Miller, Laura M</au><au>Berry, Karen K</au><au>Harper, Timothy W</au><au>Barrish, Joel C</au><au>Hollenbaugh, Diane L</au><au>Iwanowicz, Edwin J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of N-[2-[2-[[3-Methoxy-4-(5-oxazolyl)phenyl]amino]-5-oxazolyl]phenyl]-N-methyl-4- morpholineacetamide as a Novel and Potent Inhibitor of Inosine Monophosphate Dehydrogenase with Excellent in Vivo Activity</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2002-05-23</date><risdate>2002</risdate><volume>45</volume><issue>11</issue><spage>2127</spage><epage>2130</epage><pages>2127-2130</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Inosine monophosphate dehydrogenase (IMPDH) is a key enzyme that is involved in the de novo synthesis of purine nucleotides. Novel 2-aminooxazoles were synthesized and tested for inhibition of IMPDH catalytic activity. Multiple analogues based on this chemotype were found to inhibit IMPDH with low nanomolar potency. One of the analogues (compound 23) showed excellent in vivo activity in the inhibition of antibody production in mice and in the adjuvant induced arthritis model in rats.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12014950</pmid><doi>10.1021/jm0105777</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Journal of medicinal chemistry, 2002-05, Vol.45 (11), p.2127-2130 |
| issn | 0022-2623 1520-4804 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Animals Antibody Formation - drug effects Arthritis, Experimental - drug therapy Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Enzyme-Linked Immunosorbent Assay Immunomodulators IMP Dehydrogenase - antagonists & inhibitors Male Medical sciences Mice Mice, Inbred BALB C Morpholines - chemical synthesis Morpholines - chemistry Morpholines - pharmacology Mycophenolic Acid - analogs & derivatives Mycophenolic Acid - pharmacology Oxazoles - chemical synthesis Oxazoles - chemistry Oxazoles - pharmacology Pharmacology. Drug treatments Rats Rats, Inbred Lew Structure-Activity Relationship |
| title | Discovery of N-[2-[2-[[3-Methoxy-4-(5-oxazolyl)phenyl]amino]-5-oxazolyl]phenyl]-N-methyl-4- morpholineacetamide as a Novel and Potent Inhibitor of Inosine Monophosphate Dehydrogenase with Excellent in Vivo Activity |
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