Aerobic oxidation of indolomorphinan without the 4,5-epoxy bridge and subsequent rearrangement of the oxidation product to spiroindolinonyl- C-normorphinan derivative
Aerobic oxidation of indolomorphinan 1 without a 4,5-epoxy bridge proceeded in the presence of platinum catalyst to give indoleninomorphinan 2 or quinolono- C-normorphinan 5. The 4-hydroxy group would play an important role in deciding the course of the reaction. Treatment of 2a with 1,8-diazabicycl...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2009-08, Vol.17 (16), p.5983-5988 |
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| creator | Fujii, Hideaki Ogawa, Ryo Ohata, Kenji Nemoto, Toru Nakajima, Mayumi Hasebe, Ko Mochizuki, Hidenori Nagase, Hiroshi |
| description | Aerobic oxidation of indolomorphinan
1 without a 4,5-epoxy bridge proceeded in the presence of platinum catalyst to give indoleninomorphinan
2 or quinolono-
C-normorphinan
5. The 4-hydroxy group would play an important role in deciding the course of the reaction. Treatment of
2a with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave spiroindolinonyl-
C-normorphinan
3a whose structure resembles that of δ opioid receptor agonist spiroindanyloxymorphone (SIOM). Boron trichloride was effective for the reverse reaction from
3a to
2a without side reaction. This practical interconversion method between hydroxyindolenine and spiroindolinone would be useful for the design and construction of drug-like compound libraries. Although the compound
3b was expected to show the selectivity for δ opioid receptor because of the structural resemblance to SIOM, it was rather selective for μ opioid receptor (μ:
K
i
=
0.75
nM; δ:
K
i
=
2.90
nM; κ:
K
i
=
13.4
nM). The result suggests that the slight difference of the spatial location of the benzene rings in these compounds may definitively affect the binding affinity for δ opioid receptor.
Indolomorphinan without 4,5-epoxy bridge
1a was easily oxidized to give indoleninomorphinan
2a. Practical interconversion between indoleninomorphinan
2a and spiroindolinonyl-
C-normorphinan
3a became possible. |
| doi_str_mv | 10.1016/j.bmc.2009.06.067 |
| format | Article |
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1 without a 4,5-epoxy bridge proceeded in the presence of platinum catalyst to give indoleninomorphinan
2 or quinolono-
C-normorphinan
5. The 4-hydroxy group would play an important role in deciding the course of the reaction. Treatment of
2a with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave spiroindolinonyl-
C-normorphinan
3a whose structure resembles that of δ opioid receptor agonist spiroindanyloxymorphone (SIOM). Boron trichloride was effective for the reverse reaction from
3a to
2a without side reaction. This practical interconversion method between hydroxyindolenine and spiroindolinone would be useful for the design and construction of drug-like compound libraries. Although the compound
3b was expected to show the selectivity for δ opioid receptor because of the structural resemblance to SIOM, it was rather selective for μ opioid receptor (μ:
K
i
=
0.75
nM; δ:
K
i
=
2.90
nM; κ:
K
i
=
13.4
nM). The result suggests that the slight difference of the spatial location of the benzene rings in these compounds may definitively affect the binding affinity for δ opioid receptor.
Indolomorphinan without 4,5-epoxy bridge
1a was easily oxidized to give indoleninomorphinan
2a. Practical interconversion between indoleninomorphinan
2a and spiroindolinonyl-
C-normorphinan
3a became possible.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2009.06.067</identifier><identifier>PMID: 19620007</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Aerobic oxidation ; Biological and medical sciences ; Catalysis ; Competitive Bidding ; Medical sciences ; Morphinan ; Morphinans - chemical synthesis ; Morphinans - chemistry ; Morphinans - pharmacology ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Opioid ; Oxidation-Reduction ; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems ; Pharmacology. Drug treatments ; Platinum - chemistry ; Rearrangement ; Receptors, Opioid, delta - agonists ; Receptors, Opioid, delta - metabolism ; Receptors, Opioid, mu - agonists ; Receptors, Opioid, mu - metabolism</subject><ispartof>Bioorganic & medicinal chemistry, 2009-08, Vol.17 (16), p.5983-5988</ispartof><rights>2009 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c447t-82a6bc112ef1f5d2bc8796f40a1fc921885bb94802a2a63c25b99b97adac94ae3</citedby><cites>FETCH-LOGICAL-c447t-82a6bc112ef1f5d2bc8796f40a1fc921885bb94802a2a63c25b99b97adac94ae3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0968089609006397$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21839305$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19620007$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fujii, Hideaki</creatorcontrib><creatorcontrib>Ogawa, Ryo</creatorcontrib><creatorcontrib>Ohata, Kenji</creatorcontrib><creatorcontrib>Nemoto, Toru</creatorcontrib><creatorcontrib>Nakajima, Mayumi</creatorcontrib><creatorcontrib>Hasebe, Ko</creatorcontrib><creatorcontrib>Mochizuki, Hidenori</creatorcontrib><creatorcontrib>Nagase, Hiroshi</creatorcontrib><title>Aerobic oxidation of indolomorphinan without the 4,5-epoxy bridge and subsequent rearrangement of the oxidation product to spiroindolinonyl- C-normorphinan derivative</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Aerobic oxidation of indolomorphinan
1 without a 4,5-epoxy bridge proceeded in the presence of platinum catalyst to give indoleninomorphinan
2 or quinolono-
C-normorphinan
5. The 4-hydroxy group would play an important role in deciding the course of the reaction. Treatment of
2a with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave spiroindolinonyl-
C-normorphinan
3a whose structure resembles that of δ opioid receptor agonist spiroindanyloxymorphone (SIOM). Boron trichloride was effective for the reverse reaction from
3a to
2a without side reaction. This practical interconversion method between hydroxyindolenine and spiroindolinone would be useful for the design and construction of drug-like compound libraries. Although the compound
3b was expected to show the selectivity for δ opioid receptor because of the structural resemblance to SIOM, it was rather selective for μ opioid receptor (μ:
K
i
=
0.75
nM; δ:
K
i
=
2.90
nM; κ:
K
i
=
13.4
nM). The result suggests that the slight difference of the spatial location of the benzene rings in these compounds may definitively affect the binding affinity for δ opioid receptor.
Indolomorphinan without 4,5-epoxy bridge
1a was easily oxidized to give indoleninomorphinan
2a. Practical interconversion between indoleninomorphinan
2a and spiroindolinonyl-
C-normorphinan
3a became possible.</description><subject>Aerobic oxidation</subject><subject>Biological and medical sciences</subject><subject>Catalysis</subject><subject>Competitive Bidding</subject><subject>Medical sciences</subject><subject>Morphinan</subject><subject>Morphinans - chemical synthesis</subject><subject>Morphinans - chemistry</subject><subject>Morphinans - pharmacology</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Opioid</subject><subject>Oxidation-Reduction</subject><subject>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</subject><subject>Pharmacology. Drug treatments</subject><subject>Platinum - chemistry</subject><subject>Rearrangement</subject><subject>Receptors, Opioid, delta - agonists</subject><subject>Receptors, Opioid, delta - metabolism</subject><subject>Receptors, Opioid, mu - agonists</subject><subject>Receptors, Opioid, mu - metabolism</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc2O0zAUhS0EYsrAA7BB3sBqUmzHcWKxGlUMII3EBtaWf26mrhI72Eln-kI8Jy6t6A7pSpal75z7cxB6S8maEio-7tZmtGtGiFwTUap9hlaUC17VtaTP0YpI0VWkk-IKvcp5RwhhXNKX6IpKUVSkXaHft5Ci8RbHJ-_07GPAscc-uDjEMaZp64MO-NHP27jMeN4C5jdNBVN8OmCTvHsArIPDeTEZfi0QZpxAp6TDA4zHXzE7ii7uU4puscUq4jz5FP-28iGGw1DhTRViurR1kPy-yPbwGr3o9ZDhzfm9Rj_vPv_YfK3uv3_5trm9ryzn7Vx1TAtjKWXQ075xzNiulaLnRNPeSka7rjFG8o4wXcjassZIaWSrnbaSa6iv0YeTbxmzrJNnNfpsYRh0gLhkJdqm5bJjBaQn0KaYc4JeTcmPOh0UJeoYjtqpEo46hqOIKNUWzbuz-WJGcBfFOY0CvD8DOls99OWM1ud_XJm_ljVpCvfpxEE5xd5DUtl6CBacT2Bn5aL_zxh_ALuKsZI</recordid><startdate>20090815</startdate><enddate>20090815</enddate><creator>Fujii, Hideaki</creator><creator>Ogawa, Ryo</creator><creator>Ohata, Kenji</creator><creator>Nemoto, Toru</creator><creator>Nakajima, Mayumi</creator><creator>Hasebe, Ko</creator><creator>Mochizuki, Hidenori</creator><creator>Nagase, Hiroshi</creator><general>Elsevier Ltd</general><general>Elsevier</general><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>20090815</creationdate><title>Aerobic oxidation of indolomorphinan without the 4,5-epoxy bridge and subsequent rearrangement of the oxidation product to spiroindolinonyl- C-normorphinan derivative</title><author>Fujii, Hideaki ; Ogawa, Ryo ; Ohata, Kenji ; Nemoto, Toru ; Nakajima, Mayumi ; Hasebe, Ko ; Mochizuki, Hidenori ; Nagase, Hiroshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c447t-82a6bc112ef1f5d2bc8796f40a1fc921885bb94802a2a63c25b99b97adac94ae3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Aerobic oxidation</topic><topic>Biological and medical sciences</topic><topic>Catalysis</topic><topic>Competitive Bidding</topic><topic>Medical sciences</topic><topic>Morphinan</topic><topic>Morphinans - chemical synthesis</topic><topic>Morphinans - chemistry</topic><topic>Morphinans - pharmacology</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Opioid</topic><topic>Oxidation-Reduction</topic><topic>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</topic><topic>Pharmacology. Drug treatments</topic><topic>Platinum - chemistry</topic><topic>Rearrangement</topic><topic>Receptors, Opioid, delta - agonists</topic><topic>Receptors, Opioid, delta - metabolism</topic><topic>Receptors, Opioid, mu - agonists</topic><topic>Receptors, Opioid, mu - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fujii, Hideaki</creatorcontrib><creatorcontrib>Ogawa, Ryo</creatorcontrib><creatorcontrib>Ohata, Kenji</creatorcontrib><creatorcontrib>Nemoto, Toru</creatorcontrib><creatorcontrib>Nakajima, Mayumi</creatorcontrib><creatorcontrib>Hasebe, Ko</creatorcontrib><creatorcontrib>Mochizuki, Hidenori</creatorcontrib><creatorcontrib>Nagase, Hiroshi</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fujii, Hideaki</au><au>Ogawa, Ryo</au><au>Ohata, Kenji</au><au>Nemoto, Toru</au><au>Nakajima, Mayumi</au><au>Hasebe, Ko</au><au>Mochizuki, Hidenori</au><au>Nagase, Hiroshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Aerobic oxidation of indolomorphinan without the 4,5-epoxy bridge and subsequent rearrangement of the oxidation product to spiroindolinonyl- C-normorphinan derivative</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2009-08-15</date><risdate>2009</risdate><volume>17</volume><issue>16</issue><spage>5983</spage><epage>5988</epage><pages>5983-5988</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Aerobic oxidation of indolomorphinan
1 without a 4,5-epoxy bridge proceeded in the presence of platinum catalyst to give indoleninomorphinan
2 or quinolono-
C-normorphinan
5. The 4-hydroxy group would play an important role in deciding the course of the reaction. Treatment of
2a with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave spiroindolinonyl-
C-normorphinan
3a whose structure resembles that of δ opioid receptor agonist spiroindanyloxymorphone (SIOM). Boron trichloride was effective for the reverse reaction from
3a to
2a without side reaction. This practical interconversion method between hydroxyindolenine and spiroindolinone would be useful for the design and construction of drug-like compound libraries. Although the compound
3b was expected to show the selectivity for δ opioid receptor because of the structural resemblance to SIOM, it was rather selective for μ opioid receptor (μ:
K
i
=
0.75
nM; δ:
K
i
=
2.90
nM; κ:
K
i
=
13.4
nM). The result suggests that the slight difference of the spatial location of the benzene rings in these compounds may definitively affect the binding affinity for δ opioid receptor.
Indolomorphinan without 4,5-epoxy bridge
1a was easily oxidized to give indoleninomorphinan
2a. Practical interconversion between indoleninomorphinan
2a and spiroindolinonyl-
C-normorphinan
3a became possible.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19620007</pmid><doi>10.1016/j.bmc.2009.06.067</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2009-08, Vol.17 (16), p.5983-5988 |
| issn | 0968-0896 1464-3391 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67574982 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Aerobic oxidation Biological and medical sciences Catalysis Competitive Bidding Medical sciences Morphinan Morphinans - chemical synthesis Morphinans - chemistry Morphinans - pharmacology Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Opioid Oxidation-Reduction Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology. Drug treatments Platinum - chemistry Rearrangement Receptors, Opioid, delta - agonists Receptors, Opioid, delta - metabolism Receptors, Opioid, mu - agonists Receptors, Opioid, mu - metabolism |
| title | Aerobic oxidation of indolomorphinan without the 4,5-epoxy bridge and subsequent rearrangement of the oxidation product to spiroindolinonyl- C-normorphinan derivative |
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