A series of novel menthol derivatives containing 1,2,4-triazole-thioether moiety were designed, synthesized, characterized structurally, and evaluated biologically to explore more potent natural ...product-based antifungal agents. The bioassay results revealed that at 50 μg/mL, some of the target compounds exhibited good inhibitory activity against the tested fungi, especially against Physalospora piricola. Compounds 5b (R = o-CH3 Ph), 5i (R = o-Cl Ph), 5v (R = m,p-OCH3 Ph) and 5x (R = α-furyl) had inhibition rates of 93.3%, 79.4%, and 79.4%, respectively, against P. piricola, much better than that of the positive control chlorothalonil. Compounds 5v (R = m,p-OCH3 Ph) and 5g (R = o-Cl Ph) held inhibition rates of 82.4% and 86.5% against Cercospora arachidicola and Gibberella zeae, respectively, much better than that of the commercial fungicide chlorothalonil. Compound 5b (R = o-CH3 Ph) displayed antifungal activity of 90.5% and 83.8%, respectively, against Colleterichum orbicalare and Fusarium oxysporum f. sp. cucumerinum. Compounds 5m (R = o-I Ph) had inhibition rates of 88.6%, 80.0%, and 88.0%, respectively, against F. oxysporum f. sp. cucumerinu, Bipolaris maydis and C. orbiculare. Furthermore, compound 5b (R = o-CH3 Ph) showed the best and broad-spectrum antifungal activity against all the tested fungi. To design more effective antifungal compounds against P. piricola, 3D-QSAR analysis was performed using the CoMFA method, and a reasonable 3D-QSAR model (r2 = 0.991, q2 = 0.514) was established. The simulative binding pattern of the target compounds with cytochrome P450 14α-sterol demethylase (CYP51) was investigated by molecular docking.
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A series of novel nopol derivatives bearing the 1,3,4-thiadiazole-thiourea moiety were designed and synthesized by multi-step reactions in search of potent natural product-based antifungal agents. ...Their structures were confirmed by FT-IR, NMR, ESI-MS, and elemental analysis. Antifungal activity of the target compounds was preliminarily evaluated by in vitro methods against
f. sp.
,
,
,
,
,
,
, and
at 50 µg/mL. All the target compounds exhibited better antifungal activity against
,
, and
. Compound
(R =
,
-Cl Ph) showed the best broad-spectrum antifungal activity against all the tested fungi. Compounds
(R =
-Me Ph),
(R =
-Pr), and
(R =
-Cl Ph) had inhibition rates of 86.1%, 86.1%, and 80.2%, respectively, against
, much better than that of the positive control chlorothalonil. Moreover, compounds
(R =
-Cl Ph) and
(R =
-CF
Ph) held inhibition rates of 80.6% and 79.0% against
and
, respectively, much better than that of the commercial fungicide chlorothalonil. In order to design more effective antifungal compounds against
, analysis of the three-dimensional quantitative structure-activity relationship (3D-QSAR) was carried out using the CoMFA method, and a reasonable and effective 3D-QSAR model (
= 0.992,
= 0.753) has been established. Furthermore, some intriguing structure-activity relationships were found and are discussed by theoretical calculation.
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A convenient and practical strategy was developed for the synthesis of carbamo(dithioperoxo)thioates through the simple dehydrogenation coupling of thiols and amines and the insertion of CS2 under ...mild reaction conditions and in the absence of oxidizing reagents. This environmentally friendly electrosynthesis method has a broad substrate scope and can produce a series of bioactive compounds. This strategy is further employed in an electrochemical continuous flow reactor for the preparation of some antifilarial activity compounds, implying its potential application.
In order to develop novel chemotherapeutic agents with potent anticancer activities, a series of dehydroabietic acid (DHA) derivatives bearing an acylhydrazone moiety were designed and synthesized by ...the condensation between dehydroabietic acylhydrazide (3) and a variety of substituted arylaldehydes. The inhibitory activities of these compounds against CNE-2 (nasopharynx), HepG2 (liver), HeLa (epithelial cervical), and BEL-7402 (liver) human carcinoma cell lines were evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay in vitro. The screening results revealed that many of the compounds showed moderate to high levels of anticancer activities against the tested cancer cell lines and some displayed similar potent inhibitory activities to the commercial anticancer drug cisplatin, while they exhibited lower cytotoxicity against normal human liver cell (HL-7702). Particularly, compound 4w, N'-(3,5-difluorobenzylidene)-2-(dehydroabietyloxy)acetohydrazide, with an IC
(50% inhibitory concentration) value of 2.21 μM against HeLa cell, was about 17-fold more active than that of the parent compound, and showed remarkable cytotoxicity with an IC
value of 14.46 μM against BEL-7402 cell. These results provide an encouraging framework that could lead to the development of potent novel anticancer agents.
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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
f. sp.
,
,
,
, and
at 50 µg/mL. Compounds
(R =
-Pr),
(R =
-NO₂ Bn), and
(R = Et) exhibited excellent antifungal activity against
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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In the search for novel compounds with both survivin inhibitory activity and fluorescence properties, 18 novel longifolene-derived tetralin pyrimidine compounds were designed using survivin as the ...target and synthesized from the sustainable natural resource longifolene. Their structures were confirmed by IR, NMR, ESIMS, and elemental analysis. The
in vitro
antiproliferative activities of the target compounds were preliminarily evaluated using the standard MTT assay against MGC-803 (human gastric cancer cell), T24 (human bladder cancer cell), HepG2 (human liver cancer cell), and A549 (human lung adenocarcinoma cell). As a result, some of the target compounds showed better antiproliferative activities than the positive control drug 5-FU, in which, compound
5m
had an IC
50
of 1.42 μM against MGC-803 and compound
5l
had an IC
50
of 1.79 μM against T24, exhibiting excellent activity. Additionally, the target compounds display moderate or even low cytotoxicity toward human normal liver cells L02. Subsequently, a reasonable and effective 3D-QSAR model was established to study the relationship between the structure of the target compounds and antiproliferative activities and was employed to construct two new compounds with potentially better activity. Meanwhile, molecular docking was performed to study the interaction mode between the compound
5m
and survivin protein. Furthermore, the target compounds with significant antiproliferative activity showed noticeable fluorescence properties.
In the search for novel compounds with both survivin inhibitory activity and fluorescence properties, 18 novel longifolene-derived tetralin pyrimidine compounds were designed using survivin as the target and synthesized from the sustainable natural resource longifolene.
The development of atom- and step-economical methods for converting hazardous CS2 into harmless chemicals is a challenging endeavor. Herein, we disclose a feasible strategy for the electrochemical ...dehydrogenative coupling of CS2 and amines with β-ketoesters, which leads to dithiocarbamate intermediates in the presence of bases. In addition, inexpensive starting materials, broad substrate scope, and compatibility with natural product moieties make this efficient and sustainable reaction practical.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UILJ, UL, UM, UPCLJ, UPUK, ZAGLJ, ZRSKP
Twenty-seven (
)- and (
)-verbenone derivatives bearing an oxime ester moiety were designed and synthesized in search of novel bioactive molecules. Their structures were confirmed by UV-Vis, FTIR, ...NMR, ESI-MS, and elemental analysis. The antifungal and herbicidal activities of the target compounds were preliminarily evaluated. As a result, compound (
)-
(R =
-pyridyl) exhibited excellent antifungal activity with growth inhibition percentages of 92.2%, 80.0% and 76.3% against
,
, and
at 50 µg/mL, showing comparable or better antifungal activity than the commercial fungicide chlorothalonil with growth inhibition of 96.1%, 75.0% and 73.3%, respectively, and 1.7-5.5-fold more growth inhibition than its stereoisomer (
)-
(R =
-pyridyl) with inhibition rates of 22.6%, 28.6% and 43.7%, respectively. In addition, seven compounds displayed significant growth inhibition activity of over 90% against the root of rape (
) at 100 µg/mL, exhibiting much better herbicidal activity than the commercial herbicide flumioxazin with a 63.0% growth inhibition. Among these seven compounds, compound (
)-
(R =
-pyridyl) inhibited growth by 92.1%, which was 1.7-fold more than its stereoisomer (
)-
(R =
-pyridyl) which inhibited growth by 54.0%.
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Seventeen novel 2-(5-amino-1-(substituted sulfonyl)-1
-1,2,4-triazol-3-ylthio)-6- isopropyl-4,4-dimethyl-3,4-dihydronaphthalen-1(2
)-one compounds were synthesized from the abundant and naturally ...renewable longifolene and their structures were confirmed by FT-IR, NMR, and ESI-MS. The in vitro cytotoxicity of the synthesized compounds was evaluated by standard MTT assay against five human cancer cell lines, i.e., T-24, MCF-7, HepG2, A549, and HT-29. As a result, compounds
,
, and
exhibited better and more broad-spectrum anticancer activity against almost all the tested cancer cell lines than that of the positive control, 5-FU. Some intriguing structure-activity relationships were found and are discussed herein by theoretical calculation.
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A series of novel acyl thiourea compounds containing
gem
-dimethylcyclopropane ring were designed and synthesized by multi-step reactions in search of novel antifungal molecules. Structures of all ...the target compounds were characterized by spectral techniques of UV–vis, FT-IR,
1
H-NMR,
13
C-NMR, and ESI–MS. The antifungal activity of the target compounds was preliminarily evaluated by agar dilution method. The antifungal bioassay revealed that, at 50 μg/mL, compounds
5h
(R =
o
-F),
5m
(R =
p
-Br), and
5n
(R =
o
-NO
2
) showed the same antifungal activity of 73.6% against
Physalospora piricola
, which was comparable than that of the positive control. Furthermore, against
Gibberella zeae
, compounds
5k
(R =
m
-Cl),
5l
(R =
m
-Br),
5m
(R =
p
-Br), and
5n
(R =
o
-NO
2
) displayed the same antifungal activity of 75.6%, and compound
5o
(R =
p
-NO
2
) displayed antifungal activity of 78.8%, which were all better than that of the positive control. The preliminary analysis of 3D-QSAR model was performed to study the effect of molecular structure on biological activity using the comparative molecular field analysis (CoMFA) method. The results showed 3D-QSAR model (
r
2
= 0.995,
q
2
= 0.503) was reasonable and effective.
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EMUNI, FIS, FZAB, GEOZS, GIS, IJS, IMTLJ, KILJ, KISLJ, MFDPS, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, SBMB, SBNM, UKNU, UL, UM, UPUK, VKSCE, ZAGLJ
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