Synthesis and Physiological Activities of Monoterpene Carboxylic Acid Esters with Pyrones

Tachibana, Shinya; Ohno, Yuki; Fujihara, Yoshihito; Okada, Yasukazu; Sugiura, Masaaki; Takagi, Shigeki; Nomura, Masato

doi:10.5650/jos.55.181

Cited by 4 publications

(2 citation statements)

References 22 publications

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“…Additionally, the synthesis of novel 4-methyl-1,2,4-triazole-thioethers [25] and N-(4-N -substitutedsulfamoyl) phenyl)myrtenamides [26] with potential antifungal and herbicidal activities were reported. Some Myrtenal-based ester derivatives are proven to have great insecticidal activity [27]. In 2015, novel Myrtenal hybrids were successfully tested as potent analgesic [28].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Cytotoxic Analysis of Novel Myrtenyl Grafted Pseudo-Peptides Revealed Potential Candidates for Anticancer Therapy

et al. 2020

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Myrtenal is a natural monoterpene isolated from essential oils of several plants and their derivates have shown to have several biological properties including cytotoxicity. The cytotoxic activity of these derivates are being investigated for their antitumor effect leading to the development of potential anticancer agents. In this study, novels Myrtenyl grafted pseudo-peptides were designed, synthesized and functionally characterized as possible therapeutic agents for cancer treatment. Thirteen novel Myrtenyl grafted pseudo-peptides were prepared in high atom economy and efficiency by a classic Ugi-4CR and sequential post-modification. Their structures were confirmed by NMR, and ESI-MS, and its cytotoxic activity was evaluated in three cancer cell lines and primary CD4+ T cells at different proliferative cycles. Our results revealed that some of these compounds showed significant cytotoxicity against human gastric, breast and colon adenocarcinoma cells lines, but not against human dermal fibroblast cell line. Moreover, from the thirteen novel myrtenyl synthesized the compound (1R,5S)-N-{[1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-N-[2-(cyclohexylamino)-2–oxoethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide (3b) proved to be the best candidate in terms of acceptable EC50, and Emax values in cancer cell lines and at inducing cytotoxicity in CD4+ T cells undergoing active proliferation, without affecting non-proliferating T cells. Overall, the synthesis and characterization of our Myrtenyl derivates revealed novel potential anticancer candidates with selective cytotoxic activity.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Cytotoxic Analysis of Novel Myrtenyl Grafted Pseudo-Peptides Revealed Potential Candidates for Anticancer Therapy

et al. 2020

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“…As a secondary metabolite associated with medicinal essential oils, myrtenal has received growing interest in the investigation for its bioactive properties and was found to exhibit a broad spectrum of activities, such as anticancer [ 5 , 6 , 7 ], antimicrobial [ 1 ], acetylcholinesterase inhibitory [ 8 ], antimalarial [ 9 ], black bean aphid repellent [ 10 ], and bark beetle semiochemical [ 11 , 12 ] activities. Also, some myrtenal-based amide derivatives were synthesized by Nomura et al, and they were found to display insecticidal, mosquito repellent, and herbicidal activities [ 13 , 14 , 15 ]. Based on its bioactive property and chemical reactivity, myrtenal deserves further study for pharmaceutical or agrochemical use.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antifungal Activity of Novel Myrtenal-Based 4-Methyl-1,2,4-triazole-thioethers

et al. 2017

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A series of novel myrtenal derivatives bearing 1,2,4-triazole moiety were designed and synthesized by multi-step reactions in an attempt to develop potent antifungal agents. Their structures were confirmed by using UV-vis, FTIR, NMR, and ESI-MS analysis. Antifungal activity of the target compounds was preliminarily evaluated by the in vitro method against Fusarium oxysporum f. sp. cucumerinum, Physalospora piricola, Alternaria solani, Cercospora arachidicola, and Gibberella zeae at 50 µg/mL. Compounds 6c (R = i-Pr), 6l (R = o-NO2 Bn), and 6a (R = Et) exhibited excellent antifungal activity against P. piricola with inhibition rates of 98.2%, 96.4%, and 90.7%, respectively, showing better or comparable antifungal activity than that of the commercial fungicide azoxystrobin with a 96.0% inhibition rate, which served as a positive control.

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Synthesis and Bioactivity of N-(4-(N′-Substituted Sulfamoyl)Phenyl)Myrtenamides Containing a Heterocycle

et al. 2018

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Synthesis and Physiological Activities of Monoterpene Carboxylic Acid Esters with Pyrones

Cited by 4 publications

References 22 publications

Synthesis and Cytotoxic Analysis of Novel Myrtenyl Grafted Pseudo-Peptides Revealed Potential Candidates for Anticancer Therapy

Synthesis and Cytotoxic Analysis of Novel Myrtenyl Grafted Pseudo-Peptides Revealed Potential Candidates for Anticancer Therapy

Synthesis and Antifungal Activity of Novel Myrtenal-Based 4-Methyl-1,2,4-triazole-thioethers

Synthesis and Bioactivity of N-(4-(N′-Substituted Sulfamoyl)Phenyl)Myrtenamides Containing a Heterocycle

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