103-34-4Relevant articles and documents
A new method for the synthesis of N,N′-thiobisamines
Dudin
, p. 1796 - 1797 (1997)
Reaction of secondary amines (morpholine and piperidine) with sulfur and iodine afforded N,N′-thiobisamines in good yields.
Synthesis and reaction of tricyclic tetrathiins and pentathiepins: Novel formation of α-disulfines
Okuma, Kentaro,Munakata, Kazunori,Tsubota, Toshiaki,Kanto, Masayuki,Nagahora, Noriyoshi,Shioji, Kosei,Yokomori, Yoshinobu
, p. 6211 - 6217 (2012)
Cyclic polysulfanes containing a norbornane skeleton (tetrathiins and pentathiepins) were synthesized by two methods. One is the sulfurization of camphor hydrazone with disulfur dichloride, and the other is the reaction of thiocamphor with disulfur dichloride. The reduction of tetrathiin with LiEt 3BH gave the corresponding dithiol that further reacted with methyl iodide to afford the corresponding methyl sulfide. Reaction of tetrathiin with (Ph3P)2PdCl2 or NiBr2 resulted in the formation of the corresponding dithiolene metal complexes. Tetrathiins were stereoselectively oxidized by m-CPBA to afford the corresponding α-disulfines.
Method for synthesizing 4,4'-dithiodimorpholine
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Paragraph 0017-0024, (2019/10/23)
The invention discloses a method for synthesizing 4,4'-dithiodimorpholine. Sulfur monochloride and morpholine are used as raw materials, anhydrous trisodium phosphate is used as an acid binding agent,the sulfur monochloride and morpholine are reacted to produce 4,4'-dithiodimorpholine and hydrochloric acid, and the anhydrous trisodium phosphate can react with the hydrochloric acid generated in the reaction to avoid the hydrochloric acid with from reacting morpholine and the morpholine from losing the reactivity. The acid binding agent anhydrous trisodium phosphate is added in the method of the invention, so the dosage of the raw material morpholine is reduced, and the production cost is saved; and the product and impurities can be separated by washing with water after the reaction is finished, so the method has the advantages of simple production, high operability, simplicity in post-treatment and industrial application values. The appearance of the obtained product is a white needlecrystal, the yield is 90% or above, the purity is 98% or above, and use requirements are met.
Exploring the structural requirements for inhibition of the ubiquitin E3 ligase breast cancer associated protein 2 (BCA2) as a treatment for breast cancer
Brahemi, Ghali,Kona, Fathima R.,Fiasella, Annalisa,Buac, Daniela,Soukupová, Jitka,Brancale, Andrea,Burger, Angelika M.,Westwell, Andrew D.
experimental part, p. 2757 - 2765 (2010/08/20)
The zinc-ejecting aldehyde dehydrogenase (ALDH) inhibitory drug disulfiram (DSF) was found to be a breast cancer-associated protein 2 (BCA2) inhibitor with potent antitumor activity. We herein describe our work in the synthesis and evaluation of new series of zinc-affinic molecules to explore the structural requirements for selective BCA2-inhibitory antitumor activity. An N(C - S)S - S motif was found to be required, based on selective activity in BCA2-expressing breast cancer cell lines and against recombinant BCA2 protein. Notably, the DSF analogs (3a and 3c) and dithio(peroxo)thioate compounds (5d and 5f) were found to have potent activity (submicromolar IC50) in BCA2 positive MCF-7 and T47D cells but were inactive (IC50 > 10 μM) in BCA2 negative MDA-MB-231 breast cancer cells and the normal breast epithelial cell line MCF10A. Testing in the isogenic BCA2 +ve MDA-MB-231/ER cell line restored antitumor activity for compounds that were inactive in the BCA2 -ve MDA-MB-231 cell line. In contrast, structurally related dithiocarbamates and benzisothiazolones (lacking the disulfide bond) were all inactive. Compounds 5d and 5f were additionally found to lack ALDH-inhibitory activity, suggestive of selective E3 ligase-inhibitory activity and worthy of further development.
Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl- N'-sulfenylureas
Sun, Ranfeng,Zhang, Yonglin,Chen, Li,Li, Yongqiang,Li, Qingshan,Song, Haibin,Huang, Runqiu,Bi, Fuchun,Wang, Qingmin
experimental part, p. 3661 - 3668 (2010/06/19)
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.
Bis(dialkylaminethiocarbonyl)disulfides as potent and selective monoglyceride lipase inhibitors
Kapanda, Coco N.,Muccioli, Giulio G.,Labar, Geoffray,Poupaert, Jacques H.,Lambert, Didier M.
experimental part, p. 7310 - 7314 (2010/07/14)
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.
STEREOCHEMICAL COURSE OF THE -SIGMATROPIC REARRANGEMENT OF SUBSTITUTED PROPARGYL N,N-DIALKYLAMIDOSULFOXYLATES. X-RAY MOLECULAR STRUCTURE OF *,(S)R*>-4--MORPHOLINE.
Baudin, Jean-Bernard,Bkouche-Waksman, Itka,Julia, Sylvestre A.,Pascard, Claudine,Wang, Yuan
, p. 3353 - 3364 (2007/10/02)
By the reaction with three N,N-dialkylamidosulfenyl chlorides 2 bearing representative sizes for the R group on the nitrogen atom, several substituted secondary propargylic alcohols (1a-f) have been converted into the corresponding pairs of diastereoisomeric allenic sulfinamides 3a-n and 3'a-j, l, m.Their ratios have been determined by 1H NMR spectroscopy and were found to depend essentially on the sizes of both the R1 and R groups of the starting materials.The stereochemistry of one pure diastereoisomer 3m has been determined by a single crystal X-ray analysis.When treated with p-toluenesulfenyl chloride, the alcohol 1f led to a major α-allenic sulfoxide 5 which was found to be identical to that prepared by unambiguous procedures from the major α-allenic sulfinamide 3m.
DITHIONITRITES: NEW TYPE OF THIONITROSO COMPOUNDS
Shermolovich, Yu. G.,Solov'ev, A. V.,Borodin, A. V.,Pen'kovskii, V. V.,Trachevskii, V. V.,Markovskii, L. N.
, p. 1433 - 1436 (2007/10/02)
Reactions of N,N-bis(trimethylsilyl)sulfenamides with sulfur dichloride were studied; they resulted in the formation of 1-adamantyl and morpholino dithionitrites, examples of a new type of thionitroso compounds.It was found that the thermal decomposition of morpholino dithionitrite leads to the formation of dimorpholino disulfide and tetrasulfur tetranitride.Quantum-chemical calculations on a number of thionitroso compounds provides an explanation of such a course of reaction of dithionitrites.
SPECTROSCOPIC PROPERTIES OF N,N'-DITHIOBISAMINES AND THEIR CYCLIC ANALOGUES N,N'-DIALKYLCYCLOTETRASULFUR-1,4-DIIMIDES
Diaz V., C.,Arancibia, A.
, p. 1 - 8 (2007/10/02)
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.
N-ARYL-ETHENESULPHENAMIDES; THERMAL TRANSFORMATION OF TWO N-(1-NAPHTHYL)-ETHENESULPHENAMIDES INTO 1H-BENZINDOLES
Baudin, Jean-Bernard,Julia, A. Sylvestre,Ruel, Odile
, p. 881 - 890 (2007/10/02)
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.
