Linked Life Data

3783577

Source:http://linkedlifedata.com/resource/pubmed/id/3783577

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
11
pubmed:dateCreated
1986-12-24
pubmed:abstractText
Potential prodrugs of the highly insoluble, diimide antitumor agent mitindomide (1b) were synthesized by several different methods. The condensation reaction between mitindomide and formaldehyde cleanly gave the stable bis(hydroxymethyl) compound 7a, which was partially soluble in water (ca. 0.8%) and showed improved activity in the P-388 screen. When this compound was treated with secondary amines, good yields of Mannich bases could be isolated. The compound from N-methylpiperazine (7b) had excellent properties and is a candidate for clinical trials. Condensation with other aldehydes gave either no reaction or compounds with poor activity. A water-soluble ester was prepared from 7a and succinic anhydride, but had reduced potency and activity. Oxidation of the double bond of 1a with ozone gave an inactive diacid, whereas the dihydro compound was as active as the olefin. When other aromatics (anisole, p-xylene, mesitylene) were photolyzed with maleimide, the resulting photoproducts were found to be inactive. Diimides from other ring system were synthesized from the corresponding anhydrides and found to be inactive. However, the bis(hydroxymethyl) derivative of one of these (12a) was active in the P-388 screen.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Nov
pubmed:issn
0022-2623
pubmed:author
pubmed:issnType
Print
pubmed:volume
29
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
2164-70
pubmed:dateRevised
2007-11-15
pubmed:meshHeading
pubmed:year
1986
pubmed:articleTitle
Synthesis of congeners and prodrugs of the benzene maleimide photoadduct mitindomide as potential antitumor agents. 2.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S.