65212-11-5

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 110-83-8 cyclohexene 
• 4099-46-1 bis(trimethylsilyl)selenide 

Downstream Products

• 57700-94-4 N-(p-methoxybenzoyl)piperidine 
• 105223-30-1 Piperidinium 4-methoxyselenobenzoate 
• 111931-78-3 Se(Se)-phenyl 4-methoxy(diseleno)perbenzoate 
• 65212-15-9 bis(4-methoxybenzoic) selenoanhydride 

Relevant academic research and scientific papers

Cytotoxicity of new selenoimine, selenonitrone, and nitrone derivatives against human breast cancer MDA-MB231 cells

A series of new nitrone, selenoimine and selenonitrone derivatives were synthesized. Nitrone and selenonitrone derivatives were synthesized through the condensation reaction between N-mono substitutedhydroxylamine and carbonyl compounds substituted with electron donating groups, such as di(4-methoxy)benzoyl diselenide, 4-(N, N-dimethylamino) benzoyl selenonitrile and 4, 4'-di(N, N- dimethylamino)benzil, afforded a variety of new nitrone and selenonitrone compounds. Selenoimine derivative was synthesized through the condensation reaction between tert-butyl amine and (4-methoxybenzoyl selenonitrile). The yield of synthesized compounds (N1, N2, N3, N4 and N5 were (66, 60, 61, 62 and 45) %, respectively. The structures of the synthesized compounds were characterized by FT-IR, 1H-NMR, 13C-NMR, and mass spectra. Cytotoxicity of selenonitrone (N1) and selenoimine (N3) derivatives against breast cancer cells (MDA-MB231) were evaluated for 24 and 48 h via MTT assay. The IC50 value of compound N1 was 1.714 and 1.897 μM for 24 h and 48 h, respectively. The IC50 value of compound N3 was 1.438 and 2.469 μM for 24 h and 48 h, respectively. The results suggested selenonitrone (N1) and selenoimine (N3) as anti-breast cancer potential lead compound with future merit investigations.

Synthesis of some new selenonitrone compounds

The carbonyl selenonitrile and dicarbonyl diselane compounds were prepared by using the inorganic reagent such as potassium selenocyanate. New nitrone compounds were synthesized from the condensation of carbonyl group in the selenocarbonyl compounds with substituted N-phenylhydroxylamine and N-benzyl hydroxylamine. The resulting products were identified by physical properties such as melting point (M.p.), retardation factor (Rf) and color. Also compounds showed the expected data in identification techniques such as FTIR, 1H NMR, 13 C NMR, mass spectroscopy and Elemental analysis (CHN). The results proved the validity of the expected chemical structures of synthesized compounds.

Organoselenosilane-mediated selective mild access to selenolesters, selenoanhydrides and diacyl diselenides

Reaction of acyl chlorides with phenylselenotrimethyl-silane promoted by TBAF afforded a mild general access to selenolesters in good yields. When acyl chlorides were reacted with bis(trimethylsilyl)selenide (HMDSS) in 2:1 or 1:1 ratio a selective entry t

Synthesis, structures, and some reactions of [(Thioacyl)thio]- and (Acylseleno)antimony and -bismuth derivatives ((RCSS)xMR 3-x1 and (RCOSe)xMR3-x1 with M=Sb, Bi and x=1-3)

A series of [(thioacyl)thio]- and (acylseleno)antimony and [(thioacyl)thio]- and (acylseleno)bismuth, i.e., (RCSS)xMR 3-x1 and (RCOSe)xMR3-x1 (M = Sb, Bi, R1 = aryl, x = 1 - 3), were synthesized in moderate to good yields by treating piperidinium or sodium carbodithioates and -selenoates with antimony and bismuth halides. Crystal structures of (4-MeC 6H4CSS)2Sb(4-MeC6H4) (9b′), (4-MeOC6H4COSe)2Sb(4-MeC 6H4) (12c′), (4-MeOC6H 4COS)2Bi(4-MeC6H4) (15c′), and (4-MeOC6H4CSS)2BiPh (18c) along with (4-MeC6H4COS)2SbPh (6b) and (4-MeC 6H4COS)3Sb (7b) were determined (Figs. 1 and 2). These compounds have a distorted square pyramidal structure, where the aryl or carbothioato (=acylthio) ligand at the central Sb- or Bi-atom is perpendicular to the plane that includes the two carbodithioato (=(thioacyl)thio), carboselenato (=acylseleno), or carbothioato ligand and exist as an enantiomorph pair. Despite the large atomic radii, the C=S...Sb distances in (RCSS)2MR1 (M = As, Sb, Bi; R1 = aryl) and the C=O...Sb distances in (RCOS)xMR3-x 1 (M = As, Sb, Bi; x = 2, 3) are comparable to or shorter than those of the corresponding arsenic derivatives (Tables 2 and 3). A molecular-orbital calculation performed on the model compounds (MeC(E)E1) 3-xMMex (M = As, Sb, Bi; E = O, S; E1 = S, Se; x = 1, 2) at the RHF/LANL2DZ level supported this shortening of C=E...Sb distances (Table 4). Natural-bond-orbital (NBO) analyses of the model compounds also revealed that two types of orbital interactions nS → σ*MC and nS → σ* MS(1) play a role in the (thioacyl)thio derivatives (MeCSS) 3-xMMex (x = 1, 2) (Table 5). In the acylthio- MeCOSMMe2 (M = As, Sb, Bi), nO → σ* MC contributes predominantly to the orbital interactions, but in MeCOSeSbMe2, none of nO → σ*MC and nO → σ*MSe contributes to the orbital interactions. The nS → σ*MC and nS → σ*MS(1) orbital interactions in the (thioacyl)thio derivatives are greater than those of nO → σ*MC and nO → σ*ME in the acylthio and acylseleno derivatives (MeCOE)3-xMMex (E = S, Se; M = As, Sb, Bi; x = 1, 2). The reactions of RCOSeSbPh2 (R = 4-MeC6H4) with piperidine led to the formation of piperidinium diphenylselenoxoantimonate(1-) (=piperidinium diphenylstibinoselenoite) (H2NC5H10) +Ph2SbSe-, along with the corresponding N-acylpiperidine (Table 6). Similar reactions of the bis-derivatives (RCOSe)2SbR1 (R, R1 = 4-MeC6H 4) with piperidine gave the novel di(piperidinium) phenyldiselenoxoantimonate(2-) (=di(piperidinium) phenylstibonodiselenoite), [(H2NC5H10)+] 2(PhSbSe2)2-, in which the negative charges are delocalized on the SbSe2 moiety (Table 6). Treatment of RCOSeSbR21 (R, R1=4-MeC6H 4) with N-halosuccinimides indicated the formation of Se-(halocyclohexyl) arenecarboselenoates (Table 8). Pyrolysis of bis(acylseleno)arylbismuth at 150° gave Se-aryl carboselenoates in moderate to good yields (Table 9).

Reactions of acyl chlorides with LiAlHSeH. Preparation of diacyl selenides, diacyl diselenides, selenocarboxylates and cyclic selenoanhydrides

Various diacyl selenides, diacyl diselenides and selenocarboxylates were synthesized by reaction of several acyl chlorides with LiAlHSeH. Reaction of diacyl chloride with LiAlHSeH afforded cyclic selenoanhydrides. In the 77Se NMR spectra, we fo

Samarium diiodide-induced reduction of elemental selenium leading to a selenolate anion species. A selective synthesis of diacyl diselenides

Elemental selenium was reduced by samarium diiodide in THF to produce selenolate anion species which reacted with acyl chlorides to give diacyl diselenides in good yields under mild and neutral conditions.