Diastereoselective Spirocyclization of C-(Alkyloxycarbonyl)formimines of 2-Substituted 1HIndole-3-ethanamines (= Tryptamines): Basic Studies. 5th Communication on Indoles,Indolenines, and Indolines

C-(Alkoxycarbonyl)formimines of type 15–18 were derived from the 2-substituted tryptamines 2 , 9 , 10 , and 11 and transformed with tosyl chloride into tricyclic 3-spiroindoles of types 19–22 (Scheme 3). The influence of the homochiral alkoxy moieties A–D on the stereochemical outcome of this reaction was studied. Good-to-excellent diastereoselectivities were observed with the (?)-8-(phenylmenth-3-yl)oxy group ( B ) as homochiral auxiliary. The structures of the tricycles 4 , (2′R,3S)- 19B , and (2′S,3R) 20C were established by X-ray analysis, the structures of the others by NOE and CD studies, and by chemical correlation. Possibilities to explain the steric course of the spirocyclizations are discussed.     

Synthesis of Naturally Occurring Pyrazine and Imidazole Alkaloids from Botryllus LeachiRID=”a”ID=”a”?Dedicated to Prof. G. M?rkl on the occasion of his 75th birthday

The synthesis of the naturally occurring and biologically active alkaloids 1 and 2, first isolated from the red ascidian Botryllus leachi by Duran et al. [1], is described and the structure proposed for Botryllazine B (1) is confirmed. The analytical data for 2-(p-hydroxybenzoyl)-4-(p-hydroxyphenyl)imidazole (2) are discussed and compared with the literature. With special emphasis of ¹H NMR data the tautomerism of aroylimidazolemethanones is described.     

Synthesis of a new palladium salt using N‐benzyl DABCO chloride and its application in Suzuki reaction

A palladium catalyst was synthesized using N‐benzyl DABCO chloride and palladium chloride. The structure of this catalyst was characterized and then the catalyst was used in Suzuki cross‐ coupling reaction of different aryl halides with arylboronic acids. All substrates afforded the corresponding products in good to high yields in the presence of low amounts of the catalyst. Under the heating conditions employed, cheaper and more available aryl chlorides gave relatively high yields in the Suzuki reaction. Copyright © 2012 John Wiley & Sons, Ltd.     

Synthesis of Naturally Occurring Pyrazine and Imidazole Alkaloids from Botryllus LeachiRID=”a”ID=”a”?Dedicated to Prof. G. M?rkl on the occasion of his 75th birthday

The synthesis of the naturally occurring and biologically active alkaloids 1 and 2, first isolated from the red ascidian Botryllus leachi by Duran et al. [1], is described and the structure proposed for Botryllazine B (1) is confirmed. The analytical data for 2-(p-hydroxybenzoyl)-4-(p-hydroxyphenyl)imidazole (2) are discussed and compared with the literature. With special emphasis of ¹H NMR data the tautomerism of aroylimidazolemethanones is described.     

Chemical characterization and anti-breast cancer effects of silver nanoparticles using Phoenix dactylifera seed ethanolic extract on 7,12-Dimethylbenz[a] anthracene-induced mammary gland carcinogenesis in Sprague Dawley male rats

The aim of the recent research was to investigate the anti-breast cancer effects of silver nanoparticles using Phoenix dactylifera seed ethanolic extract (AgNPs). After preparation of Phoenix dactylifera seed extract, GC/MS was performed to detect the compounds. The findings indicated that 9-Octadecenoic acid (Z)- methyl ester (40.95%) and Dodecanoic acid methyl ester (20%) were the most frequent constituents found in P. dactylifera. These nanoparticles were spherical with a size range of 17-19 nm and characterized using various analytical techniques including UV–Vis absorption spectroscopy to determine the presence of AgNPs in the solution. We studied functional groups of P. dactylifera extract in the reduction and capping process of AgNPs by FT-IR, crystallinity and FCC planes by X-ray diffraction (XRD) pattern and surface morphology, shapes, and size of AgNPs by scanning electron microscopy (SEM) and transmission electron microscopy (TEM). DPPH free radical scavenging test was used to test the antioxidant properties of P. dactylifera and AgNPs, which revealed high antioxidant potential similar to butylated hydroxy toluene (BHT) as the positive control. The results of cytotoxicity analysis indicated that P. dactylifera and AgNPs were toxic for MCF-7 cells. In vivo design, induction of breast cancer was done by 7,12-Dimethylbenz[a] anthracene (DMBA) in 50 animals. After 10 days, the animals were randomly divided into six subgroups, including healthy control, untreated control, two groups receiving the P. dactylifera at 2 and 6 mg/kg and two groups receiving the AgNPs at 2 and 6 mg/kg concentrations. Both doses of P. dactylifera and AgNPs (especially AgNPs6) significantly (p ≤ 0.05) reduced the weight and volume of liver, mammary gland, kidney, spleen, ALP, AST, ALT, GGT, cholesterol, LDL, triglyceride, total and conjugated bilirubin, urea, creatinine, glucose, ferrous, ferritin, erythropoietin, GR, IL1, IL6, IL12, IL18, IFNY, and TNFα and increased HDL, total protein, albumin, WBC, lymphocyte, neutrophils, platelet, RBC, Hb, PCV, MCV, MCH, MCHC, SOD, CAT, GPx, IL4, IL5, IL10, IL13, and IFNα compared to the untreated group. Moreover, P. dactylifera and AgNPs (especially AgNPs6) significantly (p ≤ 0.05) treated breast cancer with reduction of organs free of metastasis compared to the untreated group. Seemingly, the AgNPs can be used for the treatment of breast cancer.     

N-Methylpiperidinium Chlorochromate Adsorbed on Alumina: A New Deoximation Reagent

Summary.  N-Methylpiperidinium chlorochromate adsorbed on alumina was found to be an efficient and selective reagent for the mild oxidative cleavage of oximes. Received March 1, 2001. Accepted March 22, 2001     

N-Methylpiperidinium Chlorochromate Adsorbed on Alumina: A New Deoximation Reagent

 N-Methylpiperidinium chlorochromate adsorbed on alumina was found to be an efficient and selective reagent for the mild oxidative cleavage of oximes.     

Synthesis Of 2'-Amino-3'-Methoxyflavone (Pd 98059)

2'-Amino-3'-methoxyflavone selectively blocks the activity of MAP kinase kinase (MEK) by inhibiting the activation of MAP kinase. This paper reports a straightforward synthesis of PD 98059 and 2-fert-butyl-8-methoxy-l,4-dihydro-quinolin-4-one.