Some Derivatives of Amidone

Shapiro, David J.

doi:10.1021/jo01157a017

Cited by 13 publications

(4 citation statements)

References 9 publications

(12 reference statements)

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“…According to the general procedure in Scheme 4, 3,3-diphenyl-propyl bro- The modification of segment D was carried out following the method outlined in Scheme 5. To investigate whether the electron-donating and withdrawing groups or larger and smaller substituents have any effect on the activities, the phenyl-substituted analogues of the lead compound 1, 23a-23e were formed from the corresponding 4-bromo-2-substituted phenyl-2-phenylbutanenitrile (22a-22e), which were prepared from benzeneacetonitrile 19 via bromination [20], Friedel-Crafts arylation, and bromoethylation. Because of the promising activity of piperazine and 4-methyl homopiperazine derivatives (3f and 3n) in the modification of segments B, we also chose to synthesize the compounds 24 and 25, which were obtained from the reactions of piperazine or 4-methyl homopiperazine with carbon disulfide and 4-bromo-2-(4-tert-butylphenyl)-2-phenylbutanenitrile (22d).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Structure‐Activity Relationships of A Novel Class of Dithiocarbamic Acid Esters as Anticancer Agent

Hou

Zhang

Wang³

et al. 2011

Archiv der Pharmazie

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Based on a novel lead compound 4-methylpiperazine-1-carbodithioic acid 3-cyano-3,3-diphenylpropyl ester 1, the systematic structural modification was carried out. All the synthesized compounds were evaluated for their in-vitro anticancer activities on four to six different cell lines at three different concentrations. Most of the tested compounds could selectively inhibit the growth of HL-60 and Bel-7402 cell lines at a medium concentration. Four compounds (3f, 3g, 3n, and 5) were selected for the IC(50) test, and the results revealed that three compounds (3g, 3n, and 5) showed almost the same or a slightly weaker activity than compound 1 against HL-60, and three compounds (3f, 3g, and 3n) showed >2-fold higher potency than compound 1 against Bel-7402. The in-vivo efficacy of 3n · HCl was evaluated with transplanted hepatocyte carcinoma 22 as an in-vivo test model. It was found that 3n · HCl could inhibit significantly the growth of tumor, and that this effect was dose-dependent. Meanwhile, the compound 3n · HCl showed low toxicity compared with compound 1 · HCl as evidenced by the little body-weight loss. These results confirmed that compound 3n · HCl is more potent than the lead compound 1 · HCl. Preliminary structure-activity relationships indicated that: a) Both nitrile group and the cyclic amine containing at least two nitrogens were indispensable moieties to keep the activity; b) substitution of the piperazine ring is unfavorable for the improvement of activity; c) the suitable linker joining the piperazinyl dithiocarboxyl and diphenylacetonitril group should be ethylene; d) a non-coplanar arrangement of the two benzene rings appears to be essential for activity.

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Section: Chemistrymentioning

confidence: 99%

Synthesis and Structure‐Activity Relationships of A Novel Class of Dithiocarbamic Acid Esters as Anticancer Agent

Hou

Zhang

Wang³

et al. 2011

Archiv der Pharmazie

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“…The modification of segment D was carried out following the method outlined in Scheme . To investigate whether the electron‐donating and withdrawing groups or larger and smaller substituents have any effect on the activities, the phenyl‐substituted analogues of the lead compound 1 , 23a–23e were formed from the corresponding 4‐bromo‐2‐substituted phenyl‐2‐phenylbutanenitrile ( 22a–22e ), which were prepared from benzeneacetonitrile 19 via bromination 20, Friedel‐Crafts arylation, and bromoethylation.…”

Section: Chemistrymentioning

confidence: 99%

Total Synthesis of Woodrosin I—Part 2: Final Stages Involving RCM and an Orthoester Rearrangement

Fürstner

Jeanjean

Razon

et al. 2002

Chemistry A European J

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The completion of the first total synthesis of the complex resin glycoside woodrosin I (1) is outlined using the building blocks described in the preceding paper. Key steps involve the TMSOTf-catalyzed coupling of diol 2 with trichloroacetimidate 3 which leads to the selective formation of orthoester 5 rather than to the expected tetrasaccharide. Diene 5, on treatment with catalytic amounts of the Grubbs carbene complex 6 or the phenylindenylidene ruthenium complex 7, undergoes a high yielding ring closing olefin metathesis reaction (RCM) to afford macrolide 8. Exposure of the latter to the rhamnosyl donor 4 in the presence of TMSOTf under "inverse glycosylation" conditions delivers compound 9 by a process involving glycosylation of the sterically hindered 2'-OH group and concomitant rearrangement of the adjacent orthoester into the desired beta-glycoside. This transformation constitutes one of the most advanced applications of the Kochetkov glycosidation method reported to date. Cleavage of the chloroacetate followed by exhaustive hydrogenation completes the total synthesis of the targeted glycolipid 1.

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“…Dehydration of the oxime by thionyl chloride in ether (13) gave the nitrile in yields of 68-71%; lower yields were obtained if unrecrystallized oxime were used (cf. 14).…”

Section: Bis-quaternariesmentioning

confidence: 99%