- Alkylation of NH-, OH-, and SH-acids in the presence of potassium carbonate: 1. Functionalization of chloromethyl group of alkoxy-substituted aromatic aldehydes
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An easily scalable, economocal, and more safe method for the preparation of 3-chloromethyl-4-methoxybenzaldehyde was developed. The latter was subjected to reactions with NH-, OH-, and SH-acids in the presence of potassium carbonate to obtain new aromatic aldehydes in high yields.
- Khachatryan,Razinov,Kolotaev,Belus?,Matevosyan
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p. 395 - 404
(2015/10/29)
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- New chalcones containing 5-fluorouracil exhibiting in vitro anti-cancer activity
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The synthesis and cytotoxicity evaluation of fourteen new chalcones containing 5-fluorouracil were introduced in which nine chalcones as Mannich bases 8a-i were synthesized from 2′-hydroxyacetophenone (1) in three steps including chloromethylation, N-alkylation and Claisen-Schmidt reactions. Other chalcones 14a-e were obtained from Click reaction between 1,3-dipropargyl-5-fluorouracil and azide derivatives of 2′,4′-dihydroxychalcone. The bio-assay results showed that 11 chalcones (excluding 8d, 8f and 8h) exhibited cytotoxicity against four human cancer cell lines including Hep-G2, RD, LU-1 and FL in which compound 14e exhibited the most potent cytotoxicity against Hep-G2, RD, LU-1 and FL with IC50 values of 1.48, 10.59, 3.64 and 7.02 μg/mL, respectively.
- Van Chinh, Luu,Hung, Truong Ngoc,Nga, Nguyen Thi,Phong, Le,Cuong, Le Huu,Chinh, Vu Tien,Kim, Soo Un,Vu, Tran Khac
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p. 251 - 261
(2015/06/23)
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- New chalcones containing nucleosides exhibiting in vitro anti-cancer activities
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Twenty-one new chalcones 9a-m (excluding 9e, 9j and 9l) and 10a-m (excluding 10j and 10l), containing nucleobases were synthesized from 2'-hydroxyacetophenone (1) by the reactions including chloromethylation, nucleophilic substitution with thymine and uracil, and Claisen-Schmidt reactions. These new chalcones were evaluated for in vitro cytotoxicity against five human cancer cell lines: SK-LU-1, Hep-G2, MCF7, SW480 and P388. The results showed that most of the tested chalcones exhibited inhibitory activity against five cancer cell lines except 10h, and 10i. Among the synthesized chalcones, compound 10c exhibited most potent cytotoxicity against MCF-7, SK-LU-1, SW480, HepG2 and P388 with IC50 values of 4.42, 4.81, 5.27, 3.67 and 4.11μg/mL, respectively.
- Van Chinh, Luu,Hung, Truong Ngoc,Nga, Nguyen Thi,Phong, Le,Huong, Le Mai,Ha, Tran Thi Hong,Kim, Soo Un,Vu, Tran Khac
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p. 534 - 545
(2014/05/20)
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- Synthesis and antimicrobial activity of chalcones containing benzotriazolylmethyl and imidazolylmethyl substituents
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Methods have been developed for the synthesis of new 1H-benzotriazol-1-ylmethyl- and 1H-imidazol-1-ylmethyl-substituted chalcones starting from 2-hydroxyacetophenone. The procedures include chloromethylation, N-alkylation, and Claisen-Schmidt condensation. The presence of an imidazole fragment on the ring A and piperazine fragment on the ring B of the resulting chalcones increases their antimicrobial activity (minimum inhibitory concentration 12.5-50.0 μg/mL), whereas introduction of a benzotriazole fragment reduces the antimicrobial activity.
- Chinh, L. V.,Hung, T. N.,Nga, N. T.,Mai, T. T. N.,Hang, T. T. N.,Tarasevich, V. A.
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p. 1767 - 1774
(2015/02/02)
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- Synthesis of tetrapyrrole nitrogen mustards with potential anti-tumor activities
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Eight porphyrin nitrogen mustards and six meso-tetraphenylporphin nitrogen mustards were synthesized. Most of the compounds possess both the chemotherapeutic and photochemotherapeutic effects on tumor.
- Chen, Zhi-Long,Wan, Wei-Qin,Chen, Jing-Rong,Zhao, Fang,Xu, De-Yu
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p. 1739 - 1745
(2007/10/03)
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- Phosphorylated derivatives of L-dopa and compositions and methods for increasing the melanin content in mammalian skin and hair
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A phosphorylated derivative of L-dopa of the formula STR1 wherein when X is STR2 wherein Z is --CH 2, N, S or a linkage other than oxygen which renders the phosphate group resistant to hydrolysis by phosphatase enzymes in tissues and biological fluids,then Y is OQ, wherein Q is H or an alkyl with one to twelve carbon atoms, orwherein X is OQ, then Y is STR3 wherein R'' is hydrogen or a pharmaceutically acceptable cation and R is a moiety which increases hydropobicity. The phosphorylated derivative of L-dopa is useful as an agent to increase the melanin content in mammalian skin and hair.
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- A SIMPLE AND INEXPENSIVE PROCEDURE FOR CHLOROMETHYLATION OF CERTAIN AROMATIC COMPOUNDS
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Reaction of a range of aromatic compounds with methoxyacetyl chloride and aluminium chloride in either nitromethane or carbon disulphide results in chloromethylation in good to excellent yield.
- McKillop, Alexander,Madjdabadi, Fereidon Abbasi,Long, David A.
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p. 1933 - 1936
(2007/10/02)
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- Transformation of Chloromethylbenzaldehydes into Corresponding (2-Nitroalkenyl-1) Benzyl Chlorides or Acetates. III
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Unter den bekannten Methoden zur Darstellung von β-Nitrosostyrenen wurde der guenstigste Weg fuer die Synthese von (2-Nitroalk-1-enyl)-derivaten des Chlormethylbenzaldehydes 1 gesucht.Die besten Resultate erhaelt man durch Umsetzung der Aldehyde 1 a-c zu den Schiff'schen Basen 2 a-c und nachfolgende Kondensation der Verbindungen 2 a-c mit Nitroalkanen in Essigsaeure bei Raumtemperatur.Bei hoeheren Temperaturen liefern diese Umsetzungen die (2-Nitroalk-1-enyl)benzylacetate der Struktur 7-10.Die Struktur des Ausgangsaldehydes 1 bestimmt die Geschwindigkeit dieser Reakt ion.Ein moeglicher Mechanismus sowie die 1H-NMR-Spektren der erhaltenen Verbindungen werden diskutiert.
- Grobelny, Damian,Witek, Stanislaw
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p. 536 - 542
(2007/10/02)
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- Styryl-diphenyl derivatives
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Compounds of the general formula R-CH=CH-W-CH=CH-R1 are described in which R and R1 are independently phenyl, diphenyl, naphthyl, indyl, tetrahydronaphthyl or acenaphthenyl and W is divalent phenyl, diphenyl, naphthyl, tetrahydronaphthyl or acenaphthenyl group, which groups may be substituted, the compounds containing at least one non-aromatic ring. Such compounds are useful as optical whitening agents, for example in textile material or paper.
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