Dicationic dithiocarbamate carbapenems with anti-MRSA activity

Imamura, Hideaki; Ohtake, Norikazu; Jona, Hideki; Shimizu, Aya; Moriya, M.; Sato, Hiroki; Sugimoto, Yuichi; Ikeura, Chinatsu; Kiyonaga, Hideo; Nakano, Masato; Nagano, Reiko; Abe, Shinnosuke; Yamada, Koji; Hashizume, Takashi; Morishima, Hajime

doi:10.1016/s0968-0896(01)00044-x

Cited by 73 publications

(27 citation statements)

References 20 publications

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“…Dithiocarbamic acid esters, a common class of organic molecules exhibit a variety of valuable biological effects, including antibacterial activity [1,2], antifungal activity [3], the ability to chelate heavy metals [4,5], and to function as NO scavengers [6]. Moreover, it was recently found that some kind of dithiocarbamic acid esters have cancer chemopreventive and anticancer action, which have received much attention.…”

Section: Introductionmentioning

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: Introductionmentioning

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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“…Previous studies showed that especially sulfur-containing derivatives exhibited promising antiproliferative efficiency towards several tumor cell lines [19,20]. Dithiocarbamates have been attracting considerable interest because of their diverse activities [21][22][23][24] and in the treatment of cancer [25,26]. Our group recently reported the synthesis of a novel thalidomide-containing dithiocarbamate moiety; several derivatives exhibited potent anti-cancer activity [27,28].…”

Section: Introductionmentioning

confidence: 98%

Synthesis, Biological Evaluation, Docking and QSAR Studies of Some Novel Naphthalimide Dithiocarbamate Analogs as Antitumor and Anti- Inflammatory Agents

Zahra¹,

Osman²,

Agwa³

et al. 2016

Med chem (Los Angeles)

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A series of novel naphthalimide dithiocarbamate 4a-f, 5a-f were efficiently synthesized via introduce dithiocarbamate and dithioate side chain onto the naphthalic anhydride core. The structures of the synthesized analogs were elucidated by spectroscopic methods, including IR, 1 H and 13 C NMR, and (ESIHRMS) techniques. The anti-cancer activities of the generated naphthalimide derivatives 4c, 4d, 4e, 4f, and 5d were evaluated against 21 tumour cell lines; inculding 10 tumor subpanels using MTT assay. Analogue 4c offer antitumor activity with an IC 50 of 10.54 µM against SKBR3 breast cancer cells. Compound 4d showed varying degrees of antitumor activities towards several tumour cell lines ranging from 21.1 to 71.7 µM. In addition to the antitumor activities; the synthesized compounds were evaluated for their in vitro anti-inflammatory activity. Compounds 4c and 4d revealed potent anti-inflammatory properties in comparison with the reference drug celecoxib. Molecular docking studies provided complementary theoretical support for experimental biological data.

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“…Dithiocarbamates exhibit important properties in many areas, such as antibacterial or antifungal activity [6,7], chelation of heavy metals [8], and nitrogen monoxide scavenging [9,10]. Our group developed a simple and convenient one-pot method for synthesis of dithiocarbamates [11].…”

Section: Introductionmentioning

confidence: 99%

LRD-22, a novel dual dithiocarbamatic acid ester, inhibits Aurora-A kinase and induces apoptosis and cell cycle arrest in HepG2 cells

Wang

et al. 2015

Biochemical and Biophysical Research Communications

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Dicationic dithiocarbamate carbapenems with anti-MRSA activity

Cited by 73 publications

References 20 publications

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

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

Synthesis, Biological Evaluation, Docking and QSAR Studies of Some Novel Naphthalimide Dithiocarbamate Analogs as Antitumor and Anti- Inflammatory Agents

LRD-22, a novel dual dithiocarbamatic acid ester, inhibits Aurora-A kinase and induces apoptosis and cell cycle arrest in HepG2 cells

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