138200-74-5

Upstream product

• 30189-89-0 N-methyl-N-hexylaniline 
• 192934-80-8 N-methyl-4-N-(4-nitrophenyl)hexanamide 
• 142-61-0 Hexanoyl chloride 
• 142-62-1 hexanoic acid 
• 66-25-1 hexanal 
• 100-15-2 N-methyl(p-nitroaniline) 

Downstream Products

• 192934-98-8 N-hexyl-N-methyl-p-phenylenediamine 

Relevant academic research and scientific papers

Reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3as a reductant

Herein, we report the first example of efficient reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3 as a catalyst and a reductant under mild conditions, affording various tertiary and secondary amines in excellent yields. A mechanistic study indicates that BH3N(C2H5)3 plays a dual function role of promoting imine and iminium formation and serving as a reductant in reductive amination. This journal is

Structure-activity relationships for the antileishmanial and antitrypanosomal activities of 1'-substituted 9-anilinoacridines

Members of the class of 9-anilinoacridine topoisomerase II inhibitors bearing lipophilic electron-donating 1'-aniline substituents are active against both the promastigote and amastigote forms of the parasite Leishmania major. A series of analogues of the known 1'-NHhexyl lead compound were prepared and evaluated against L. major in macrophage culture to further develop structure-activity relationships (SAR). Toxicity toward mammalian cells was measured in a human leukemia cell line, and the ratio of the two IC50 values (IC50(J)/IC50(L)) was used as a measure of the in vitro therapeutic index (IVTI). A 3,6-diNMe2 substitution pattern on the acridine greatly increased toxicity to L. major without altering mammalian toxicity, increasing IVTIs over that of the lead compound. The 2-OMe, 6-C1 acridine substitution pattern used in the antimalarial drug mepacrine also resulted in potent antileishmanial activity and high IVTIs. Earlier suggestions of the utility of 2'-OR groups in lowering mammalian cytotoxicity were not borne out in this wider study. A series of very lipophilic 1'-NRR (symmetric dialkylamino)-substituted analogues showed relatively high antileishmanial potency, but no clear trend was apparent across the series and none were superior to the 1'-NH(CH2)5Me subclass. Subsets of the most active 1'- N(R)(CH2)5Me- and 1'-N(alkyl)2-substituted compounds against L. major were also evaluated against Leishmania donovani, Trypanosoma cruzi, and Trypanosoma brucei, but no consistent SAR could be discerned in these physiologically diverse test systems. The present study has confirmed earlier conclusions that lipophilic electron-donating groups at the 1'-position of 9- anilinoacridines provide high activity against L. major, but the SAR patterns observed do not carry over to the other parasites studied.

N-Dealkylation-N-nitrosation of Tertiary Aromatic Amines by n-Butyl Nitrite

N,N-Dialkyl aromatic amines with a variety of ring substituents are N-dealkylated and N-nitrosated efficiently by n-butyl nitrite/ammonium chloride/water at reflux temperature.Ring nitrosation was never observed, but minor amounts of m- and p-nitro amines and/or nitrosamines were formed in some cases.Ring nitration is rather a reaction of the initial substrate than a process occurring on formed nitrosamines.The leaving propensities of the initial N-substituents to yield nitrosamines were in the order benzyl >> methyl >> alkyl.Key Words: Nitrosamines; N-Dealkylation; N-Nitrosation; C-Nitration; Alkyl nitrite.