Uro-Angiographic Contrast Agents—The Holy Grail
Christoph de Haën in X-Ray Contrast Agent Technology, 2019
In analogy to the esterification of the carboxyl group in known ionic triiodinated contrast agents, amidation of the kind that was to become the basis for breakthrough nonionic compounds was contemplated. The industrially practical preparation of the acid chloride intermediates bearing acylated aniline functions posed an unexpected obstacle. These difficulties constituted a hurdle significant enough to impede for a while continued exploration in that direction. It is noteworthy that the value of nonionic molecules as uro-angiographic contrast agents was not fully recognized until much later and thus at this time the motivation for overcoming the synthetic difficulties was low. Since the economic circumstances at the time were not favorable for the industrial development of uro-angiographic novelties (see Section “Perfecting Ionic Uro-Angiographic Contrast Agents”), pursuit of nonionicity did not acquire importance for many more years.
Proteins for Conditioning Hair and Skin
Randy Schueller, Perry Romanowski in Conditioning Agents for Hair and Skin, 2020
Building on the development of hydrolyzates, a variety of condensation products were then generated and evaluated for application in personal care (4,8). Reaction of fatty acid chloride (RCOC1, R = C8-C18) with primary amino groups of the hydrolyzate in alkaline media attached the R group via an amide linkage to the hydrolyzate. These hydrolyzates thus became anionic surfactants. Depending on the length of the polypeptide chain and the identity of the R group, mild wetting, foaming, conditioning, plasticizing, and emulsifying properties were achieved. Neutralized C12 and C14 versions (e.g., TEA-lauroyl hydrolyzed collagen) behaved similarly to synthetic detergent but with much less eye and skin irritation. Their C16 and C18 counterparts (e.g., potassium stearoyl hydrolyzed collagen) behaved similarly to soaps.
Hepatotoxic and Hepatocarcinogenic Effects of Chlorinated Ethylenes*
Robert G. Meeks, Steadman D. Harrison, Richard J. Bull in Hepatotoxicology, 2020
It is known that the initial oxidation is followed by a preferential chlorine migration and subsequent formation of an aldehyde or an acid chloride, which can be further metabolized to an acid or an alcohol (Bonse and Henschler, 1976). The formation of an unstable reactive acid chloride is one reactive intermediate which binds cellular macromolecules. Dekant et al. (1987) identified the majority of alkylated macromolecules arising from PCE metabolism as N-trichloroacetylated phospholipids. Phospholipid adducts have also been identified following administration of TCE or VCD (Reichert et al., 1979; Dekant et al., 1984). Conjugation of reactive intermediates with glutathione is also known to occur for the chlorinated ethylenes and plays the major role in VDC toxicity, as will be discussed later (Allemand et al., 1978; Liebler et al., 1985).
Folate receptor-targeted mixed polysialic acid micelles for combating rheumatoid arthritis: in vitro and in vivo evaluation
Published in Drug Delivery, 2018
Nan Zhang, Chunyu Xu, Na Li, Shasha Zhang, Lingling Fu, Xiao Chu, Haiying Hua, Xianghui Zeng, Yongxing Zhao
FTIR spectrums indicated hydroxyl and amide functional group and of PSA around 3400 and 1650 cm−1, respectively. CC showed featured acyl chloride peak at 1790 cm−1, carbon–hydrogen bond at 2950 cm−1, and double peaks for C(CH3)2 at 1400 cm−1. Successful conjugation of CC to PSA destroyed acyl chloride group and resulted in the peak disappearance at 1790 cm−1. (Figure 1(A)) NMR result of PSA-CC also confirmed the appearance of hydrogens that belonged to CC at 0.5–1.5 ppm. (Supplementary Figure S1) CMC results indicated that PSA-CC and FA-PSA-CC started to form micelles at the concentration of 46.2 ± 3.9 and 32.1 ± 5.2 μg/mL, respectively (Supplementary Figure S2(A,B)). TEM showed a round shape of PSA-CC and FA-PSA-CC micelles with the size 80–100 nm (Figure 1(B,C)). TEM results were consistent with dynamic light scattering results. The size of PSA-CC and FA-PSA-CC micelles was 93.8 ± 13.4 and 83.8 ± 13.4 nm respectively using zeta-sizer. Both of PSA-CC and FA-PSA-CC micelles showed a sufficient negative charge and small PDI, indicating a high stability in solution (Supplementary Figure S2(C)). With Dex loading, the size of PSA-CC and FA-PSA-CC micelles increased slightly (Supplementary Figure S3).
Design, synthesis and biological activity of selective hCAs inhibitors based on 2-(benzylsulfinyl)benzoic acid scaffold
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2019
Giulia Rotondi, Paolo Guglielmi, Simone Carradori, Daniela Secci, Celeste De Monte, Barbara De Filippis, Cristina Maccallini, Rosa Amoroso, Roberto Cirilli, Atilla Akdemir, Andrea Angeli, Claudiu T. Supuran
The reaction of the ester 45 with hydroxylamine hydrochloride in methanol at room temperature for 48 h gave the N-hydroxy benzamide 5126. Compounds 47–49 were obtained converting the carboxylic acids 39–41 to the corresponding acyl chlorides by means of oxalyl chloride in the presence of a catalytic amount of dry DMF. Acyl chlorides were subsequently treated with ammonium hydroxide (NH4OH), to afford the desired amides (Scheme 4)27. The amide 50 was obtained by a different route (Scheme 5). At first, it was synthesised the amide from the anthranilic acid activated by SOCl2 in DMF at room temperature as previously reported. The addiction of NaH and phenylacetyl chloride in dry THF at room temperature let to the final amide 50.
Selenium-analogs based on natural sources as cancer-associated carbonic anhydrase isoforms IX and XII inhibitors
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2023
Nora Astrain-Redin, Niccolò Paoletti, Daniel Plano, Alessandro Bonardi, Paola Gratteri, Andrea Angeli, Carmen Sanmartin, Claudiu T. Supuran
The synthesis method of the compounds is shown in Scheme 1. The synthesis procedure and the characterisation of the compounds were described in our previous study.30 Briefly, hydrogen sodium selenide (NaHSe) was formed by the reduction of elemental Se with NaBH4 in water. Then, the corresponding acid chloride was added to the reaction mixture to form the corresponding sodium selenoate by a nucleophilic acyl substitution. Finally, the target compounds were obtained through a nucleophilic substitution over the allyl/propargyl bromide. All the compounds were purified by column chromatography.
Related Knowledge Centers
- Acetyl Chloride
- Carboxylic Acid
- Functional Group
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- Organic Compound
- Side Chain
- Acyl Halide
- Moiety
- Carbonyl Group
- Hydrochloric Acid