Convenient synthesis of 10H-indolo[3,2-b]quinolines and 6H-indolo[2,3-b]quinolines by sequential chemoselective Suzuki reaction followed by double C-N coupling

A convenient and regioselective synthesis of two series of indolo[2,3-b]quinolines, namely 10H-indolo[3,2-b]quinolines and 6H-indolo[2,3-b]quinolines, has been developed. The synthesis, proceeds in moderate to high yields, involving chemoselective palladium catalyzed Suzuki reaction of 2,3-dihaloquinolines with 2-bromophenylboronic acid, followed by a double Buchwald-Hartwig C-N coupling.     

Molecular Complexes of Crown Ethers: Part 7. Effect of Surfactant on the Charge-Transfer Complex between Dibenzo-18-Crown-6 and Tetracyanoethylene

The charge transfer complexes (CTC) of dibenzo-18-crown-6 (DB 1 8C6) andtetracyanoethylene (TCNE) were studied in the presence of the surfactant TritonX-100. It was found that the stability of the CTC increases with increasingconcentration of the donor, acceptor and the surfactant. This suggests that thecharge transfer complex is encapsulated in the micelle structure. Results of theeffect of time on the complex stability are also presented.     

Characterization of oligosaccharide moieties of glycopeptides by microwave-assisted partial acid hydrolysis and mass spectrometry

Microwave-assisted partial acid hydrolysis and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry were used to study oligosaccharide structures of glycopeptides. Tryptic N-glycosylated peptides of horseradish peroxidase, with MH+ ions at m/z 2533, 2612, 3355, 3673, and 5647, were used as test cases. Within a microwave exposure with trifluoroacetic acid of 2 min, partial cleavages of the oligosaccharides of these tryptic N-glycosylated peptides were observed. The data showed that the most labile group within the oligosaccharides is the fucose (Fuc) residue, and that a majority of the end cleavage products are peptides with one N-acetylglucosamine (GlcNAc) residue linked to asparagine (Asn). In addition, the glycopeptides with m/z 3355 and 3673 carry an oligosaccharide (Xyl)Man3(Fuc)GlcNAc2, the glycopeptide at m/z 5647 carries two oligosaccharides (Xyl)Man3(Fuc)GlcNAc2, and the glycopeptides at m/z 2612 and 2533 carry (Xyl)Man3GlcNAc2 and (Fuc)GlcNAc, respectively. However, the glycosylation site of the m/z 2612 peptide at Asn286 is partially occupied. This simple and rapid method is particularly useful in identifying glycopeptides and obtaining monosaccharide compositions of glycopeptides.     

Synthesis and Antimycobacterial Activity of New 2-Hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.4]non-4-yl)/(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2,2-diphenylacetamide Derivatives

Summary. 2-Hydroxy-2,2-diphenylacetohydrazide (2), cyclic ketones, and mercaptoalkanoic acids were converted into 2-hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.4]non/[4.5]dec-4-yl)-2,2-diphenylacetamide derivatives (3, 4) in a one pot procedure. Compounds 3 and 4 were tested for in vitro antimycobacterial activity against M. tuberculosis H37Rv. The compounds were found to provide 0–86% inhibition of mycobacterial growth in the primary screen conducted at 6.25 μg/cm³.     

H and D release in approximately 243.1 nm photolysis of vibrationally excited 3nu1, 4nu1, and 4nuCD overtones of propyne-d3

The photofragmentation of propyne-d(3), D(3)C-C[Triple Bond]C-H, following approximately 243.1 nm photodissociation of rovibrationally excited molecules promoted to the second (3nu(1)) and third (4nu(1)) acetylenic C-H overtone and to the third (4nu(CD)) methyl overtone has been investigated. The resulting H and D photoproducts were detected via (2+1) resonantly enhanced multiphoton ionization. The measured room-temperature photoacoustic and jet-cooled action spectra allowed derivation of the molecular parameters of the C-H overtones and the Doppler profiles revealed the translational energies associated with the H(D) photofragments and the H to D branching ratios. Propensities toward the latter were encountered, while the translational energy disposal in both photofragments was essentially identical for a given preexcitation. This behavior agrees with that found for the almost isoenergetic 193.3 nm photolysis of propyne [Qadiri et al., J. Chem. Phys. 119, 12842 (2003)], but contradicts previous findings. The bond fission of C-H and C-D is preceded by internal conversion to, and isomerization on, the ground-state potential energy surface (PES), followed by extensive intramolecular vibrational redistribution. For molecules preexcited to 3nu(1) and 4nu(1) an additional minor channel opens, where elimination of H occurs directly on the accessed excited PES, while that of D on the ground state.     

A convenient and new approach to the synthesis of ω-heterocyclic amino acids from carboxy lactams through ring-chain-transformation. Part 2: Synthesis of (2R)-/(2S)-2-aminomethyl-3-(1-aryl-/1,5-diaryl-1H-pyrazol-3-yl)-propionic acid

Making use of amide activation, a convenient and short path synthesis of optically pure ω-heterocyclic-β-amino acids has been achieved from (1R,3R)- and (1R,3S)-5-oxo-1-(1-phenyl-ethyl)-pyrrolidine-3-carboxylic acid methyl ester. The key step of the synthesis involves a regiospecific ring-chain-transformation of the enaminones when subjected to 1,2-binucleophilic attacks. The method is illustrated by the synthesis of (2R)-/(2S)-2-aminomethyl-3-(1-aryl-/1,5-diaryl-1H-pyrazol-3-yl)-propionic acid.     

Comparative Chemical Profiles of the Essential Oils from Different Varieties of Psidium guajava L.

Guava (Psidium guajava) leaves are commonly used in the treatment of diseases. They are considered a waste product resulting from guava cultivation. The leaves are very rich in essential oils (EOs) and volatiles. This work represents the detailed comparative chemical profiles of EOs derived from the leaves of six guava varieties cultivated in Egypt, including Red Malaysian (RM), El-Qanater (EQ), White Indian (WI), Early (E), El-Sabahya El-Gedida (ESEG), and Red Indian (RI), cultivated on the same farm in Egypt. The EOs from the leaves of guava varieties were extracted by hydro-distillation and analyzed with GC-MS. The EOs were categorized in a holistic manner using chemometric tools. The hydro-distillation of the samples yielded 0.11–0.48% of the EO (v/w). The GC-MS analysis of the extracted EOs showed the presence of 38 identified compounds from the six varieties. The sesquiterpene compounds were recorded as main compounds of E, EQ, ESEG, RI, and WI varieties, while the RM variety attained the highest content of monoterpenes (56.87%). The sesquiterpenes, β-caryophyllene (11.21–43.20%), and globulol (76.17–26.42%) were detected as the major compounds of all studied guava varieties, while trans-nerolidol (0.53–10.14) was reported as a plentiful compound in all of the varieties except for the RM variety. A high concentration of D-limonene was detected in the EOs of the RM (33.96%), WI (27.04%), and ESEG (9.10%) varieties. These major compounds were consistent with those reported for other genotypes from different countries. Overall, the EOs’ composition and the chemometric analysis revealed substantial variations among the studied varieties that might be ascribed to genetic variability, considering the stability of the cultivation and climate conditions. Therefore, this chemical polymorphism of the studied varieties supports that these varieties could be considered as genotypes of P. guajava. It is worth mentioning here that the EOs, derived from leaves considered to be agricultural waste, of the studied varieties showed that they are rich in biologically active compounds, particularly β-caryophyllene, trans-nerolidol, globulol, and D-limonene. These could be considered as added value for pharmacological and industrial applications. Further study is recommended to confirm the chemical variations of the studied varieties at a molecular level, as well as their possible medicinal and industrial uses.     

Highly sensitive high-performance thin-layer chromatography method for the simultaneous determination of molnupiravir,favipiravir, and ritonavir in pure forms and pharmaceutical formulations

Favipiravir, molnupiravir, and ritonavir have been recently approved as the first oral antivirals for treatment of SARS-CoV-2 viral infections. Their combination was reported in several clinical studies, alternatively, to enhance the viral eradication and improve patient's recovery times and rates. Being all orally administered, therefore, the development of new sensitive and validated methodologies for their simultaneous determination is a necessitate. In the proposed research, a sensitive, selective, and simple high-performance thin layer chromatography method was developed and validated for determination of favipiravir, molnupiravir, and ritonavir. Silica gel 60F254 thin layer chromatography plates were used as stationary phase for this separation using mobile phase composed of methylene chloride:ethyl acetate:methanol:25% ammonia (6:3:4:1, v/v/v/v). Densitometric detection was performed at wavelength 289 nm. Peaks of favipiravir, molnupiravir, and ritonavir were resolved at retention factors 0.22, 0.42, and 0.63, respectively. The proposed method was found linear within the specified ranges of 3.75–100.00 μg/mL for molnupiravir and favipiravir, and 2.75–100.00 μg/mL for ritonavir. Limits of detection were found to be 1.12, 1.21, and 0.89 μg/mL for favipiravir, molnupiravir, and ritonavir, respectively. This is the first method to be reported for the simultaneous determination of the cited three antiviral drugs. The method was assessed on novel greenness metrics.     

SiGe optoelectronic metal-oxide semiconductor field-effect transistor

We propose a novel semiconductor optoelectronic switch that is a fusion of a Ge optical detector and a Si metal-oxide semiconductor field-effect transistor (MOSFET). The device operation is investigated with simulations and experiments. The switch can be fabricated at the nanoscale with extremely low capacitance. This device operates in telecommunication standard wavelengths, hence providing the surrounding Si circuitry with noise immunity from signaling. The Ge gate absorbs light, and the gate photocurrent is amplified at the drain terminal. Experimental current gain of up to 1000x is demonstrated. The device exhibits increased responsivity (approximately 3.5x) and lower off-state current (approximately 4x) compared with traditional detector schemes.