- Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl- N'-sulfenylureas
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Aseries of new N'-alkylaminothio,N'-arylaminothio (or dithio), and N',N'-thio (or dithio) derivatives ofN'-benzoyl-N'-phenylureas were designed and synthesized as insect-growth regulators with sulfur dichloride or disulfur dichloride as the original reactant. The new compounds were identified by 1H nuclear magnetic resonancee (NMR) spectroscopy, elemental analysis [or high-resolution mass spectrometry (HRMS)], and single-crystal X-ray diffraction analysis. The X-ray results demonstrated that there exist N-S-N or N-S-S-N bonds in these new compounds. In comparison to the parent N-benzoyl-N'-phenylureas, these derivatives displayed better solubility. The insecticidal activities of the target compounds were evaluated. The results of bioassays showed that compounds 1-24 retained the larvicidal activities of the corresponding benzoylphenylureas (BPUs) and some compounds exhibited better larvicidal activities against oriental armyworm and mosquitoes than the parent BPUs. The larvicidal activities of the selected target compounds 1 and 24 against diamondback moth were better than that of the corresponding parent compounds E and triflumuron.
- Sun, Ranfeng,Zhang, Yonglin,Chen, Li,Li, Yongqiang,Li, Qingshan,Song, Haibin,Huang, Runqiu,Bi, Fuchun,Wang, Qingmin
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experimental part
p. 3661 - 3668
(2010/06/19)
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- Bis(dialkylaminethiocarbonyl)disulfides as potent and selective monoglyceride lipase inhibitors
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Monoglyceride lipase (MGL) inhibition may offer an approach in treating diseases in which higher 2-arachidonoyglycerol activity would be beneficial. We report here the synthesis and pharmacological evaluation of bis(dialkylaminethiocarbonyl)disulfide derivatives as irreversible MGL inhibitors. Inhibition occurs through interactions with MGL C208 and C242 residues, and these derivatives exhibit high inhibition selectivity over fatty acid amide hydrolase, another endocannabinoid-hydrolyzing enzyme. 2009 American Chemical Society.
- Kapanda, Coco N.,Muccioli, Giulio G.,Labar, Geoffray,Poupaert, Jacques H.,Lambert, Didier M.
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experimental part
p. 7310 - 7314
(2010/07/14)
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- Method of treating a disease condition caused or exacerbated by an HPV
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The invention provides agents and compounds (see (I) and (II)) for use in the treatment or prophylaxis of disease conditions caused or exacerbated by mammalian papillomaviruses, such as human papillomaviruses, as well as methods for the treatment or prevention thereof. In said formulae, R1–R4 and n are as defined herein.
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Page/Page column 17-18
(2008/06/13)
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- Inactivation of the human papillomavirus-16 E6 oncoprotein by organic disulfides
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We are investigating compounds that could be useful in the treatment of neoplastic lesions of the cervix by acting on the oncoprotein E6 of human papillomavirus-16. The E6 protein contains two potential zinc-binding domains that are required for most of its functions. We have published tests that measure (i) the release of zinc ions after chemical alteration of the cysteine groups of these zinc-binding domains (TSQ assay), (ii) the interaction of E6 with the cellular proteins E6AP and E6BP (BIACORE assay), and (iii) the viability of tumor cell lines that require the continuous expression of HPV oncoproteins (WST1 assay). Based on these tests, we identified 4,4'-dithiodimorpholine as a potential lead compound. In this study we examined whether the dithiobisamine moiety of 4,4'-dithiodimorpholine may be an important molecular prerequisite for further drug development in this system. We have evaluated 59 new substances including organic disulfides and those containing the dithiobisamine moiety, as well as structural analogues. The compounds with significant reactivity in all three assays were observed only for dithiobisamine derivatives with saturated cyclic amines and aryl substituted piperazines. The identity of these substances suggests that the N-S-S-N moiety is necessary but not sufficient for reactivity in our assays, and that dithiobisamine based substances are useful as lead compounds that target the cysteine groups of HPV-16 E6 zinc fingers. Copyright (C) 2000 Elsevier Science Ltd.
- Beerheide, Walter,Sim, Mui Mui,Tan, Yee-Joo,Bernard, Hans-Ulrich,Ting, Anthony E
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p. 2549 - 2560
(2007/10/03)
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- A new method for the synthesis of N,N′-thiobisamines
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Reaction of secondary amines (morpholine and piperidine) with sulfur and iodine afforded N,N′-thiobisamines in good yields.
- Dudin
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p. 1796 - 1797
(2007/10/03)
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- SPECTROSCOPIC PROPERTIES OF N,N'-DITHIOBISAMINES AND THEIR CYCLIC ANALOGUES N,N'-DIALKYLCYCLOTETRASULFUR-1,4-DIIMIDES
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A series of N,N'dithiobisamines R2N-S-S-NR2 NR2=N(CH3)2, N(CH2CH3)2, pipreridine, morpholine, N(CH2-C6H5)2 and N,N'-dialkylcyclotetrasulfur-1,4-diimides (RN)2S4R=CH3, C6H11, CH2C6H5 has been prepared and their 1H-NMR, IR, and UV spectra measured.The proton chemical shifts and the ν(S-N) frequency data are consistent with a chain open conformation for R2N-S-S-NR2 and with a cyclic structure for (RN)2S4.From UV spectral data, values of the disulfide dihedral angle were estimated and a strucrture for the compound proposed.
- Diaz V., C.,Arancibia, A.
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- N-ARYL-ETHENESULPHENAMIDES; THERMAL TRANSFORMATION OF TWO N-(1-NAPHTHYL)-ETHENESULPHENAMIDES INTO 1H-BENZINDOLES
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Reaction of vinylmagnesium bromide with morpholine or piperidine-N-sulphenyl chlorides 3a,b affords the N-ethenylthio-morpholine and -piperidine 4a,b.When treated with stoichiometric amounts of an arylamine and methanesulphonic (or trifluoroacetic) acid, the sulphenamides 4 are converted into N-aryl-ethenesulphenamides 6a-e.On heating in toluene, two of these sulphenamides 6d and 6e undergo -sigmatropic rearrangements followed by cyclisation of the intermediate amino-thioaldehydes yielding the corresponding 1H-benzindoles 8a,b.
- Baudin, Jean-Bernard,Julia, A. Sylvestre,Ruel, Odile
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p. 881 - 890
(2007/10/02)
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- A NEW PREPARATION OF N-ARYL-1-ALKYNESULPHENAMIDES AND THEIR THERMAL REARRANGEMENTS INTO INDOLINE-2-THIONES
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Reaction of 1-alkynyl-lithio derivatives with N,N-dialkylaminosulphenyl chlorides 3a,b affords the N,N-dialkyl-1-alkynesulphenamides 4.When treated with stoichiometric amounts of a substituted benzenamine and methanesulfonic (or trifluoroacetic) acid, the sulphenamides 4, are converted into N-aryl-1-alkynesulphenamides 6-20.On heating in benzene, many of these sulphenamides 6-20 undergo -sigmatropic rearrangements followed by cyclisation of the intermediate thioketenes yielding the substituted indoline-2-thiones 21-30.
- Baudin, Jean-Bernard,Julia, Sylvestre A.,Lorne, Robert
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p. 181 - 188
(2007/10/02)
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