Design, synthesis, and antitumor evaluation of novel naphthalimide derivatives

Li, Xin; Wu, Zheng; Xu, Lu; Chi, Chun-Lan; Chen, Baoquan

doi:10.1007/s00044-019-02471-w

Cited by 6 publications

(2 citation statements)

References 47 publications

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“…exhibited its best activity against L929 (IC50 = 0.22 μM). In comparison with standard chemotherapeutic drugs, such as 5-fluorouracil (5-FU) (IC50 = 2.98 µM against L929, 16 and 11.40 µM against MDA-MB-231 17 ), and cisplatin (IC50 = 7.84 µM against SiHa, and 19.13 µM against MDA-MB-231), 18 the studied compounds seem to be of relevance for their antiproliferative activity. In general, the new derivatives 2-6 did not overcome the cytotoxic activity of the natural product 1, which, as mentioned above, possesses a γ,δ-unsaturated carbonyl system that appears to be important for its activity as an alkylating agent.…”

Section: Scheme 1 Preparation Of Seco-oxacassane Derivatives 2-6 Starting From Natural Diterpenoidmentioning

confidence: 99%

Uncommon Reactivity of a Seco-Oxacassane Diterpenoid and Antiproliferative Activity of Some Derivatives

Torres-Valencia¹,

Hernández-Jiménez²,

De-la-Cruz-Martínez³

et al. 2021

HETEROCYCLES

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The main diterpenoid of Acacia schaffneri, 7,8-seco-7,8-oxacassa-13,15-dien-7-ol-17-al (1), has two aldehydes of which one is protected as a ε-lactol.The free aldehyde resisted to afford the carboxylic acid using reagents with different oxidative strength, although 1 gave oxime 2 when treated with hydroxylamine, β-hydroxyketone 3 after addition of acetone, aldo-ε-lactone 4 whereby only the lactol was oxidized when using Jones reagent, and epoxyformate 5 after Baeyer-Villiger treatment. Hydrolysis of 5 with NaHCO3 gave 6. Structures 2-6 followed from physical and spectral data including X-ray diffraction. All compounds showed antiproliferative activity similar to some chemotherapeutic drugs against C2C12, L929, SiHa, and MDA-MB-231 cell lines. RESULTS AND DISCUSSIONDiterpenoid 1 was obtained in adequate amounts for the preparation of 2-6 from the aerial parts of A.schaffneri. 1 Nucleophilic addition of hydroxylamine to 1 gave 2 in 66% yield, while aldol condensation of 1 with acetone in basic medium led to β-hydroxyketone 3 in 43% yield. The corresponding 1 H NMR spectra did not evidence both syn and anti oximes for 2, nor the absolute configuration (AC) of C-17 in the case of 3. However, the anti oxime geometry in 2 and the (17S) AC in 3 followed from the X-ray diffraction (XRD) studies detailed below. Although 3 was not the only expected condensation product, the γ,δ-unsaturated carbonyl compound could not be obtained even when using large excesses of acetone and NaOH.

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Section: Scheme 1 Preparation Of Seco-oxacassane Derivatives 2-6 Starting From Natural Diterpenoidmentioning

confidence: 99%

Uncommon Reactivity of a Seco-Oxacassane Diterpenoid and Antiproliferative Activity of Some Derivatives

Torres-Valencia¹,

Hernández-Jiménez²,

De-la-Cruz-Martínez³

et al. 2021

HETEROCYCLES

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“…Efficacy of disulfide linkers as compare to other linkers against several tumor xenografts in pre-clinical models has been proved 2 . In various chemical and biological agents that show potent reactivity or possess pharmacological activities like anti-tumor activities, disulfide bond (-S-S-) is an extremely valuable functional group 3,9 . It has already been detected that various proteins, oxidized glutathione, and numerous naturally obtained products, including some drugs i.e., Mitomycin, leinamycin consists of disulfide bond 10,11 .…”

Section: Introductionmentioning

confidence: 99%

Untitled

2022

IJPSR

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To increase the efficacy of present anti-tumor agents, tumor-targeting can be proved as a successful approach for effective and safer drug delivery with less toxicity. According to researchers, for an effective tumor targeting module, disulfide linkage plays an important role in providing a medium for conjugating an anti-tumor drug with a carrier like vitamins and fatty acids. Disulfide bonds with unique chemical and biophysical properties can be used as cleavable linkers to deliver chemotherapeutic drugs. From the literature review, it has been observed that a disulfide bond acts as a self-immolating linker, which gets cleaved inside the body in the presence of intracellular glutathione; otherwise, it is stable in blood circulation. In this review, we discussed various strategies available in literature using disulfide as a linker in potent tumor targeting agents. Various successful conjugates are described here, which are currently under clinical trials.

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Design, synthesis, antiproliferative and antimicrobial evaluation of a new class of disulfides containing 1,3,4-thiadiazole units

Zhang

Chi

et al. 2022

Med Chem Res

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Design, synthesis, and antitumor evaluation of novel naphthalimide derivatives

Cited by 6 publications

References 47 publications

Uncommon Reactivity of a Seco-Oxacassane Diterpenoid and Antiproliferative Activity of Some Derivatives

Uncommon Reactivity of a Seco-Oxacassane Diterpenoid and Antiproliferative Activity of Some Derivatives

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Design, synthesis, antiproliferative and antimicrobial evaluation of a new class of disulfides containing 1,3,4-thiadiazole units

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