Synthesis of acetylenic ketones from straight-chain acid chlorides

Background: Agro-waste derived solvent media act as a greener process for the peptide bond formation using Nα - Fmoc-amino acid chloride and amino acid ester salt with in situ neutralization and coupling under biphasic condition. The Fmoc-amino acid chlorides are prepared by the reported procedure of freshly distilled SOCl2 with dry CH2Cl2. The protocol found many added advantages such as neutralization of amino acid ester salt and not required additional base for the neutralization, and directly coupling take place with Fmoc-amino acid chloride gave final product dipeptide ester in good to excellent yields. The protocol occurs with complete stereo chemical integrity of the configuration of substrates. Here, we revisited Schotten-Baumann condition, instead of using inorganic base. Objective: To develop green protocol for the synthesis of peptide bond using Fmoc-amino acid chloride with amino acid esters salt. Methods: The final product isolated is analyzed in several spectroscopic and analytical techniques such as FT-IR, 1H-, 13CNMR, Mass spectrometry and RP-HPLC to check stereo integrity and purity of the product. Conclusion: The present method developed greener using natural agro-waste (lemon fruit shell ash) derived solvent medium for the reaction and not required chemical entity.

Download Full-text

Noncataleptic neuroleptic agents: 2-(4-(2-(2-Chloro-10,11-dihydrodibenzo[b,f]thiepin-10-yloxy)ethyl)piperazine-1-yl)ethanol and some related compounds

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19882731 ◽

1988 ◽

Vol 53 (11) ◽

pp. 2731-2741 ◽

Cited By ~ 2

Author(s):

Jiří Jílek ◽

Martin Valchář ◽

Jiří Holubek ◽

Nataša Dlohožková ◽

Josef Pomykáček ◽

...

Keyword(s):

Preclinical Studies ◽

Acid Chlorides ◽

Substitution Reactions ◽

Related Compounds

10-(2-Bromoethoxy)-2-chloro-10,11-dihydrodibenzo[b,f]thiepin (X), prepared by two methods, was subjected to substitution reactions with 2-(1-piperazinyl)ethanol, 3-(1-piperazinyl)propanol, 1-methylpiperazine, 3-(1-piperazinyl)propionamide, piperazine, and 1-(ethoxycarbonyl)piperazine and gave the title compounds II-VII. The alcohol II was esterified by treatment with acid chlorides to compounds VIII and IX. Compounds II, V, and VIII proved to be noncataleptic neuroleptic agents and II (clopithepin, VÚFB-17 076) was selected for preclinical studies.

Download Full-text

Substituted N,N-Dimethyl-3-(phenylthio)- and -4-(phenylthio)benzylamines

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19920194 ◽

1992 ◽

Vol 57 (1) ◽

pp. 194-203 ◽

Cited By ~ 5

Author(s):

Karel Šindelář ◽

Vojtěch Kmoníček ◽

Marta Hrubantová ◽

Zdeněk Polívka

Keyword(s):

Serotonin Receptors ◽

Hydrobromic Acid ◽

Antidepressant Activity ◽

Benzoic Acids ◽

Lithium Aluminium Hydride ◽

Acid Chlorides ◽

Activity Inhibition ◽

Lithium Aluminium ◽

The Brain

(Arylthio)benzoic acids IIa - IIe and VIb - VId were transformed via the acid chlorides to the N,N-dimethylamides which were reduced either with diborane "in situ" or with lithium aluminium hydride to N,N-dimethyl-(arylthio)benzylamines Ia - Ie and Vb - Vd. Leuckart reaction of the aldehydes IX and X with dimethylformamide and formic acid afforded directly the amines Va and Ve. Demethylation of the methoxy compounds Ia and Ve with hydrobromic acid resulted in the phenolic amines If and Vf. The most interesting N,N-dimethyl-4-(phenylthio)benzylamine (Va) hydrochloride showed affinity to cholinergic and 5-HT2 serotonin receptors in the rat brain and some properties considered indicative of antidepressant activity (inhibition of serotonin re-uptake in the brain and potentiation of yohimbine toxicity in mice).

Download Full-text

Polycondensation of Triphosphonitrilic Amides with Dibasic Acid Chlorides

The Journal of the Society of Chemical Industry Japan ◽

10.1246/nikkashi1898.70.8_1453 ◽

1967 ◽

Vol 70 (8) ◽

pp. 1453-1454 ◽

Cited By ~ 1

Author(s):

Masaaki YOKOYAMA ◽

Sakae KONYA

Keyword(s):

Dibasic Acid ◽

Acid Chlorides

Download Full-text

Lipidomics of facial sebum in the comparison between acne and non-acne adolescents with dark skin

Scientific Reports ◽

10.1038/s41598-021-96043-x ◽

2021 ◽

Vol 11 (1) ◽

Author(s):

Obumneme Emeka Okoro ◽

Adebomi Adenle ◽

Matteo Ludovici ◽

Mauro Truglio ◽

Federico Marini ◽

...

Keyword(s):

Relative Abundance ◽

Building Blocks ◽

Carbon Chain ◽

Gas Chromatography Mass Spectrometry ◽

Lower Percentage ◽

Void Space ◽

Straight Chain ◽

Dark Skin ◽

Cross Sectional ◽

Weight Percentage

AbstractLipidomics is advantageous in the study of sebum perturbations occurring in acne. An extended evaluation of the sebum lipid profiles in acne-prone sebaceous areas is lacking in dark skin. Yet, there is a void space in understanding how the building blocks of sebum lipids, i.e. individual fatty acids (FAs), are intertwined with acne-prone skin. We aimed to determine the sebum lipidome in facial areas of adolescents with and without acne in Nigeria. A cross-sectional analytical study was conducted in 60 adolescents/young adults divided in 30 acne patients (15F, 15M) and 30 age and sex-matched controls. Sebum samples obtained from foreheads and cheeks were analysed separately by gas chromatography–mass spectrometry (GCMS) and thin layer chromatography (HPTLC). Distributions of sebum components were investigated with multivariate ANOVA-simultaneous component analysis (ASCA). Sebum incretion in acne was paralleled by significantly higher abundance of triglycerides, wax esters, and squalene together with monounsaturated FAs (MUFAs), and straight chain saturated FAs (SFAs), especially those with odd-carbon chain, i.e. C13:0, C15:0, and C17:0. Profiling weight/weight percentage of individual components revealed that, in acne, the free FAs (FFAs) array was shifted towards higher relative abundance of the SFAs C15:0, C16:0, and C17:0 and lower percentage of the anteiso-branched FFAs with 12, 14, 16, and 18 carbons. In acne patients, MUFAs and PUFAs were quantitatively increased and decreased on foreheads and cheeks, respectively. Relative abundance of fatty alcohols was decreased in acne independent on the site. The results indicated that acne associates with site-specific derangement of the pathways regulating the balance among odd straight-chain and branched-chain SFAs, MUFAs, which included sapienate (C16:1n-10), PUFAs, and squalene.

Download Full-text