78178-56-0Relevant academic research and scientific papers
Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products
Tangdenpaisal, Kassrin,Worayuthakarn, Rattana,Karnkla, Supatra,Ploypradith, Poonsakdi,Intachote, Pakamas,Sengsai, Suchada,Saimanee, Busakorn,Ruchirawat, Somsak,Chittchang, Montakarn
, p. 925 - 937 (2015/03/31)
Despite the therapeutic potential of marine-derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug-like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully devised to construct a library of 59 systematically designed lamellarin analogs, which were then subjected to cytotoxicity and log P determinations. Along with the 25 first-generation lamellarins previously synthesized in our laboratory, the structure-activity and structure-lipophilicity relationships were extensively evaluated. Our results clearly indicated the additional structural requirements around the lamellarin skeleton which, when combined with those reported previously, can provide invaluable guidance for further modifications to increase the aqueous solubility of these compounds.
BIOSYNTHESIS OF TYLOPHORINE AND TYLOPHORININE
Bhakuni, Dewan S.,Mangla, Virendra K.
, p. 401 - 407 (2007/10/02)
Administration of 3,4-dihydroxyphenyl(2-(14)C)alanine to young Tylophora asthmatica plants revealed that ring B and carbon atoms C9 and C7' of tylophorine and tylophorinine are derived from dopa.Tracer experiments with 6,7-diphenylhe
Biosynthesis. Part 24. Speculative Incorporation Experiments with 1-Benzylisoquinolines and a Logical Approach via C6-C2 and C6-C3 Precursors to the Biosynthesis of Hasubanonine and Protostephanine
Battersby, Alan R.,Jones, Raymond C. F.,Kazlauskas, Rymantas,Thornber, Craig W.,Ruchirawat, Somsak,Staunton, James
, p. 2016 - 2029 (2007/10/02)
Many possible 1-benzyltetrahydroisoquinolines have been examined as possible advanced precursors of the alkaloids hasubanonine (1) and protostephanine (2) in Stephania japonica plants, but none was incorporated significantly.Administration of various precursor molecules having only one aromatic ring, such as tyrosine, has demonstrated that both alkaloids are derived from two different C6-C2 biogenetic units.The subsequent failure of further 1-benzyltetrahydroisoquinolines and bisphenethylamines to be incorporated suggested the intermediacy of either (a) modified 1-benzylisoquinolines or (b) trioxygenated C6-C2 building blocks.Precursors designed to examine the first possibility, such as 1-benzyl-3,4-dihydroisoquinolines or 1-benzyl-1-carboxytetrahydroisoquinolines, were not incorporated into (1) and (2) whereas two 3',4',5'-trioxygenated 2-phenylethylamines were incorporated.These findings allow further delineation of the requirements for later precursors of the alkaloids (1) and (2).
Biosynthesis. Part 25. Proof that Hasubanonine and Protostephanine are Biosynthesised from the 1-Benzylisoquinoline System
Battersby, Alan R.,Jones, Raymond C. F.,Minta, Akwasi,Ottridge, Anthony P.,Staunton, James
, p. 2030 - 2039 (2007/10/02)
The syntheses are described of a set of sixteen 1-benzylisoquinolines and four bisphenethylamines built from 2-(3,4-dihydroxy-5-methoxyphenyl)ethylamine (3), a known biosynthetic precursor to the alkyloids hasubanonine (1) and protostephanine (2) in Steph
Synthesis of Substituted 6,7-Diphenyl-1,2,3,5,8,8a-hexahydroindolizines
Mangla, V. K.,Bhakuni, D. S.
, p. 931 - 937 (2007/10/02)
Substituted 6,7-diphenyl-1,2,3,5,8,8a-hexahydroindolizines (28a to 28e) have been synthesized by two methods.In first method, condensation of substituted 2-phenacylpyrrolidines (24b to 24d) with substituted phenylacetylchlorides (2) affords substituted 2-
