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Synthesis and pharmacological evaluation of a new class of bicyclic phospholipids, designed as platelet activating factor antagonists
(±)-3-Alkoxymethyl-(2-oxabicyclo[3.3.0]octane)-5-yl-methyl-phosphoryl-ethyl-pyridinium [alkyl chain=methyl ( 5a) and ( 5b), allyl ( 6a) and ( 6b), n-propyl ( 7a) and ( 7b) and n-hexyl ( 8a) and (8b)] derivatives, structurally designed as conformationally restricted platelet activating factor (PAF) a...
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| Published in: | Farmaco (Società chimica italiana : 1989) 1998-05, Vol.53 (5), p.327-336 |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c389t-c3d30f55edf47b3dddc73c62545c81e98819c3647a0c6fdad83b50f0f5e089b33 |
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| cites | cdi_FETCH-LOGICAL-c389t-c3d30f55edf47b3dddc73c62545c81e98819c3647a0c6fdad83b50f0f5e089b33 |
| container_end_page | 336 |
| container_issue | 5 |
| container_start_page | 327 |
| container_title | Farmaco (Società chimica italiana : 1989) |
| container_volume | 53 |
| creator | Peçanha, Emerson Poley Fraga, Carlos Alberto Manssour Sant'Anna, Carlos Maurício Rabello de de Miranda, Ana Luisa Palhares Barreiro, Eliezer Jesus |
| description | (±)-3-Alkoxymethyl-(2-oxabicyclo[3.3.0]octane)-5-yl-methyl-phosphoryl-ethyl-pyridinium [alkyl chain=methyl (
5a) and (
5b), allyl (
6a) and (
6b),
n-propyl (
7a) and (
7b) and
n-hexyl (
8a) and (8b)] derivatives, structurally designed as conformationally restricted platelet activating factor (PAF) antagonists were synthesized in 12–26% overall yield, using ethyl (±)-3-hydroxymethyl-5-(2-oxabicyclo[3.3.0] octane) carboxylate (
13a,b) as key intermediate. The anti-platelet profile of the new derivatives was evaluated in a PAF-induced aggregation model in rabbit platelet-rich plasma; only compound
8a exhibited a modest activity. |
| doi_str_mv | 10.1016/S0014-827X(98)00027-5 |
| format | article |
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5a) and (
5b), allyl (
6a) and (
6b),
n-propyl (
7a) and (
7b) and
n-hexyl (
8a) and (8b)] derivatives, structurally designed as conformationally restricted platelet activating factor (PAF) antagonists were synthesized in 12–26% overall yield, using ethyl (±)-3-hydroxymethyl-5-(2-oxabicyclo[3.3.0] octane) carboxylate (
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5a) and (
5b), allyl (
6a) and (
6b),
n-propyl (
7a) and (
7b) and
n-hexyl (
8a) and (8b)] derivatives, structurally designed as conformationally restricted platelet activating factor (PAF) antagonists were synthesized in 12–26% overall yield, using ethyl (±)-3-hydroxymethyl-5-(2-oxabicyclo[3.3.0] octane) carboxylate (
13a,b) as key intermediate. The anti-platelet profile of the new derivatives was evaluated in a PAF-induced aggregation model in rabbit platelet-rich plasma; only compound
8a exhibited a modest activity.</description><subject>2-Oxabicyclo[3.3.0]octane system</subject><subject>Animals</subject><subject>Antithrombotic activity</subject><subject>Biological and medical sciences</subject><subject>Blood. Blood coagulation. Reticuloendothelial system</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Phospholipids - chemical synthesis</subject><subject>Phospholipids - pharmacology</subject><subject>Platelet activating factor (PAF) antagonists</subject><subject>Platelet Activating Factor - antagonists & inhibitors</subject><subject>Platelet Aggregation Inhibitors - chemical synthesis</subject><subject>Rabbits</subject><issn>0014-827X</issn><issn>1879-0569</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><recordid>eNqFkc2KFDEUhYMoY8_oIwxkIaJgaapSVUlWIoOjwoCLUXAXUsmtnkg6KXPTLf0Avrfp6WZcusjP5Z5zbvhCyGXL3rasHd_dMtb2jezEj1dKvmaMdaIZHpFVK4Vq2DCqx2T1IHlKzhF_1lKIUZyRMzUK1cluRf7c7mO5A_RITXR0uTN5Y2wKae2tCRR2JmxN8SnSNFNDI_ymNhjEQzl5u7fB2-pKWFfwi3f4hroat47gqEG6BFMgQKHGFr-rSXFN53pPuc4rZp2ix4LPyJPZBITnp_OCfL_--O3qc3Pz9dOXqw83jeVSlbo7zuZhADf3YuLOOSu4HbuhH6xsQUnZKsvHXhhmx9kZJ_k0sLlagEk1cX5BXh5zl5x-bQGL3ni0EIKJkLaoJWN8HFVbhcNRaHNCzDDrJfuNyXvdMn3Ar-_x6wNbraS-x6-H6rs8DdhOG3APrhPv2n9x6husfOdsovX4L7z-Dhd9lb0_yqDC2HnIGq2HaMH5DLZol_x_HvIXBVilYw</recordid><startdate>19980530</startdate><enddate>19980530</enddate><creator>Peçanha, Emerson Poley</creator><creator>Fraga, Carlos Alberto Manssour</creator><creator>Sant'Anna, Carlos Maurício Rabello de</creator><creator>de Miranda, Ana Luisa Palhares</creator><creator>Barreiro, Eliezer Jesus</creator><general>Elsevier SAS</general><general>Elsevier Science</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>19980530</creationdate><title>Synthesis and pharmacological evaluation of a new class of bicyclic phospholipids, designed as platelet activating factor antagonists</title><author>Peçanha, Emerson Poley ; Fraga, Carlos Alberto Manssour ; Sant'Anna, Carlos Maurício Rabello de ; de Miranda, Ana Luisa Palhares ; Barreiro, Eliezer Jesus</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-c3d30f55edf47b3dddc73c62545c81e98819c3647a0c6fdad83b50f0f5e089b33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>2-Oxabicyclo[3.3.0]octane system</topic><topic>Animals</topic><topic>Antithrombotic activity</topic><topic>Biological and medical sciences</topic><topic>Blood. Blood coagulation. Reticuloendothelial system</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Phospholipids - chemical synthesis</topic><topic>Phospholipids - pharmacology</topic><topic>Platelet activating factor (PAF) antagonists</topic><topic>Platelet Activating Factor - antagonists & inhibitors</topic><topic>Platelet Aggregation Inhibitors - chemical synthesis</topic><topic>Rabbits</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Peçanha, Emerson Poley</creatorcontrib><creatorcontrib>Fraga, Carlos Alberto Manssour</creatorcontrib><creatorcontrib>Sant'Anna, Carlos Maurício Rabello de</creatorcontrib><creatorcontrib>de Miranda, Ana Luisa Palhares</creatorcontrib><creatorcontrib>Barreiro, Eliezer Jesus</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>Farmaco (Società chimica italiana : 1989)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Peçanha, Emerson Poley</au><au>Fraga, Carlos Alberto Manssour</au><au>Sant'Anna, Carlos Maurício Rabello de</au><au>de Miranda, Ana Luisa Palhares</au><au>Barreiro, Eliezer Jesus</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and pharmacological evaluation of a new class of bicyclic phospholipids, designed as platelet activating factor antagonists</atitle><jtitle>Farmaco (Società chimica italiana : 1989)</jtitle><addtitle>Farmaco</addtitle><date>1998-05-30</date><risdate>1998</risdate><volume>53</volume><issue>5</issue><spage>327</spage><epage>336</epage><pages>327-336</pages><issn>0014-827X</issn><eissn>1879-0569</eissn><abstract>(±)-3-Alkoxymethyl-(2-oxabicyclo[3.3.0]octane)-5-yl-methyl-phosphoryl-ethyl-pyridinium [alkyl chain=methyl (
5a) and (
5b), allyl (
6a) and (
6b),
n-propyl (
7a) and (
7b) and
n-hexyl (
8a) and (8b)] derivatives, structurally designed as conformationally restricted platelet activating factor (PAF) antagonists were synthesized in 12–26% overall yield, using ethyl (±)-3-hydroxymethyl-5-(2-oxabicyclo[3.3.0] octane) carboxylate (
13a,b) as key intermediate. The anti-platelet profile of the new derivatives was evaluated in a PAF-induced aggregation model in rabbit platelet-rich plasma; only compound
8a exhibited a modest activity.</abstract><cop>Lausanne</cop><pub>Elsevier SAS</pub><pmid>9679282</pmid><doi>10.1016/S0014-827X(98)00027-5</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0014-827X |
| ispartof | Farmaco (Società chimica italiana : 1989), 1998-05, Vol.53 (5), p.327-336 |
| issn | 0014-827X 1879-0569 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_80036691 |
| source | ScienceDirect Freedom Collection 2022-2024 |
| subjects | 2-Oxabicyclo[3.3.0]octane system Animals Antithrombotic activity Biological and medical sciences Blood. Blood coagulation. Reticuloendothelial system Medical sciences Pharmacology. Drug treatments Phospholipids - chemical synthesis Phospholipids - pharmacology Platelet activating factor (PAF) antagonists Platelet Activating Factor - antagonists & inhibitors Platelet Aggregation Inhibitors - chemical synthesis Rabbits |
| title | Synthesis and pharmacological evaluation of a new class of bicyclic phospholipids, designed as platelet activating factor antagonists |
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