Synthesis, NMR Characterization, and Antileukemic Activity of N-Nonanoylpiperazinyl-5α-Androstane-3α,17β-Diol A-Ring Derivatives

The combination of an androstane-3,17-diol nucleus and a 2β-N-alkylamidopiperazino sidechain is important for the anticancer activity of a new family of steroid derivatives. As the structure-activity relationship studies have so far been limited to the beta orientation of the substituent at position 2 of the steroid nucleus, a series of analogs (compounds 1–4) were synthesized to investigate the impact on biological activity of A-ring substitution. Nuclear magnetic resonance (NMR) analysis, especially using a series of 2D experiments, such as correlation spectroscopy (COSY), homonuclear Overhauser effect spectroscopy (NOESY), heteronuclear single-quantum correlation (HSQC), and heteronuclear multiple-bond correlation (HMBC) provided crucial information that was found essential in confirming the sidechain position and orientation of compounds 1–4. Assessment of their antiproliferative activity on leukemia HL-60 cells confirmed the best efficiency of the 2β-sidechain/3α-OH orientation (compound 1) compared to the other configurations tested (compounds 2–4).

Chemical Constituents of Tagetes patula and Their Neuroprotecting Action

Two novel flavonoids (1, 2) and 3 known compounds (3-5) were isolated from the flowers and whole plant of Tagetes patula L., and their structures were elucidated by means of ultra-high performance liquid chromatography with electrospray ionization, coupled to quadrupole-time-of-flight/mass spectrometry, 1H and 13C-nuclear magnetic resonance (NMR), as well as 2-dimensional-NMR (heteronuclear single quantum correlation and heteronuclear multiple bond correlation) and chemical methods. In addition, all the compounds were examined for their neuroprotective action on the injury of SH-SY5Y cells induced by glutamate, indicating that the protective effect of these compounds on glutamate-induced SH-SY5Y cell was marigold biflavone > patuletin > quercetin > kaempferol-3- O-β-d-glucoside > patuletin-3- O-α-l-arabinopyranoside. Thus, it could be concluded that flavonoids played a key role in the neuroprotective action of T. patula.

Synthesis and Photoelectrical Properties of 3-(Diphenylamino)Carbazolyl-Functionalized DMABI Derivatives

A modular approach was used in the synthesis of the 3-(diphenylamino)carbazolyl- functionalized 2-(4-(dimethylamino)benzylidene)-1H-indene-1,3(2H)-dione (DMABI) derivatives. For this purpose, carboxyl functional group was introduced into the framework of DMABI molecule. Additionally, a regioselective method for substitution of carbonyl group of DMABI with dicyanomethylene group was investigated and verified using the heteronuclear multiple bond correlation NMR spectra. Steglich esterification method was used to connect the 3‑(diphenylamino)carbazolyl moiety via an unconjugated spacer. The UV-Vis absorption spectra and molecular energy level data were obtained for the evaluation of the synthesized compounds as donor materials in bulk-heterojunction solar cells.

5-(6-Hydroxy-6-methyl-5-oxoheptan-2-yl)-2-methyl Phenyl Acetate

We synthesized a novel compound, 5-(6-hydroxy-6-methyl-5-oxoheptan-2-yl)-2-methylphenyl acetate, in a good yield by oxidation of 1-O-acetyl-xanthorrizol using potassium permanganate in acidic condition. The structure was elucidated by Fourier Transform Infrared (FTIR), 1H-Nuclear Magnetic Resonance (NMR) and 13C-NMR, two-dimensional (2D)-HSQC, Distortionless Enhancement by Polarization Transfer (DEPT), 2D-Heteronuclear Multiple Bond Correlation (HMBC), and High-Resolution Mass Spectra (HRMS) spectral data.

A novel norneolignan glycoside and four new phenolic glycosides from the stems of Viburnum fordiae Hance

A novel norneolignan glycoside (1), categorized as an unusual 7-noraryl-4′,7-epoxy-8,5′-neolignan glycoside, four new phenolic glycosides (2–5), and a known neolignan glycoside (6) have been isolated from the ethanolic extract of the stems ofViburnum fordiaeHance. Dried stems ofV. fordiaewere extracted with 95% ethanol, and the concentrated extract was portioned successively with petroleum ether, ethyl acetate andn-butanol. Then-butanol portion was subjected to the macroporous resin HPD-100, silica gel, octadecyl SiO2, MCI gel and Sephadex LH-20 columns to obtain six compounds. Their structures including absolute configurations were determined by spectroscopic data [1H and13C nuclear magnetic resonance (NMR), total correlation spectroscopy (TOCSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple-bond correlation (HMBC) and optical rotatory dispersion (ORD)] and chemical methods.

Synthesis and structure analysis of polyesteramides modified with bio-based diaminopentane hexanedioic salt

Two series of bio-based diaminopentane hexanedioic salt (DHS) modified polyesteramides were successfully synthesized by two different synthesis processes in which DHS reacted with bis-hydroxyethyl terephthalate (BHET) and low molecular weight polyester (LPET), respectively. The intrinsic viscosities of the polyesteramides ranged from 0.62 dl/g to 0.78 dl/g, which correlated greatly with the requirements of subsequent processing such as spinning. The results of the heteronuclear multiple bond correlation (HMBC) indicated that the diaminopentane segment was directly connected with the purified terephthalic acid (PTA) segment. The presence of ester and amide group characteristic peaks in the Fourier transform-infrared (FT-IR) spectroscopy confirmed that the final resultant products were polyesteramides. The results of elemental analysis showed that the ratio of actual nitrogen content to theoretical nitrogen content of two series of polyesteramides was 76%~90%, and the actual nitrogen content in both series was proportional to the addition of DHS.