1694-01-5Relevant academic research and scientific papers
n-alkylamino analogs of Vitamin K3: Electrochemical, DFT and anticancer activity of their oxidized and one electron reduced form
Chadar, Dattatray,Banerjee, Priyabrata,Saha, Sourav Kr.,Bhand, Sujit,Patil, Rajendra,Salunke-Gawali, Sunita
, p. 443 - 452 (2019)
Synthesis, characterization and anticancer activity of reduced form of n-alkylamino analogs of Vitamin K3 (1Na to 8Na) are undertaken. Molecular structure and molecular association of oxidized form of 2-ethylamino-3-methyl-1,4-naphthoquinone (2) and 2-hexylamino-3-methyl-1,4-naphthoquinone (6) were studied by single crystal X-ray analysis. 2 crystallize in monoclinic C2/c and 6 in P21 space group. The reduced form of eight homologated analogs of 2-(n-alkylamino)-3-methyl-1,4-naphthoquinone (1Na to 8Na) were synthesized using sodium metal as reductant at 0 °C in methanol. The formations of naphthosemiquinone radical in 1 to 6 have been confirmed from their EPR spectra. Polycrystalline powder X-band EPR spectra of 1 to 6 shows signals ～2.0020 ± 0.0026 at 133 K. Anticancer activity of 2-(n-alkylamino)-3-methyl-1,4-naphthoquinone (1Na to 8Na) and one electron reduced forms have been evaluated against breast cancer (HeLa) cell line, 1 and 1Na showed promising anticancer activity.
PHOTOLYSIS OF 2-DIALKYLAMINO-3-METHYL-1,4-NAPHTHOQUINONES
Bukhtoyarova, A. D.,Berezhnaya, V. N.,Shishina, R. P.,Vetchinov, V. P.,Eroshkin, V. I.,Stavitskaya, T. A.
, p. 2094 - 2098 (1991)
The photolysis of 2-dialkylamino-1,4-naphthoquinones is significantly more efficient when a methyl group is at C3.The quantum yields are 2-6 times greater than for 2-dialkylaminonaphthoquinones lacking a methyl group. 2-Monoalkylamino-1,4-naphthoquuinones also undergo photochemical dealkylation.
Synthesis and characterization of n-alkylamino derivatives of vitamin K3: Molecular structure of 2-propylamino-3-methyl-1,4-naphthoquinone and antibacterial activities
Chadar, Dattatray,Camilles, Maria,Patil, Rishikesh,Khan, Ayesha,Weyhermüller, Thomas,Salunke-Gawali, Sunita
, p. 179 - 189 (2015)
We would like to introduce eight analogues of n-alkylamino derivatives of vitamin K3 (2-methyl-1,4-naphthoquinone) viz, 2-(n-alkylamino)-3-methyl-1,4-naphthoquinone (where n-alkyl is methyl; LM-1, ethyl; LM-2, propyl; LM-3, butyl; LM-4, pentyl; LM-5, hexyl; LM-6, heptyl; LM-7, octyl; LM-8). All the above analogues have been successfully synthesized from vitamin K3 and characterized using different analytical techniques. Furthermore, in order to understand the mechanistic aspects of formation of LM-1 to LM-8 compounds, we could propose the mechanism. The FT-IR analysis of LM-1 to LM-8 indicate the presence of characteristic band of NH group ～3287-3364 cm-1, the variation was attributed to extensive intramolecular hydrogen bonding interaction. The molecular structure of LM-3 compound has been confirmed by single crystal X-ray diffraction analysis. LM-3 compound crystallises in triclinic space group P1. There were four independent molecules in asymmetric unit cell and their molecular interactions observed via NH.
IDO inhibitor, preparation method and applications thereof
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Paragraph 0155-0158; 0293-0296, (2020/04/17)
The invention relates to an IDO inhibitor, a preparation method and applications thereof, and belongs to the technical field of medicinal chemistry. The IDO inhibitor with the characteristics of a structure represented by a general formula I or the pharma
Synthesis, antibacterial and antifungal activity of 2-amino-1,4- naphthoquinones using silica-supported perchloric acid (HClO4- SiO2) as a mild, recyclable and highly efficient heterogeneous catalyst
Sharma, Upendra,Katoch, Deepali,Sood, Swati,Kumar, Neeraj,Singh, Bikram,Thakur, Archana,Gulati, Arvind
, p. 1431 - 1440 (2014/01/06)
Perchloric acid adsorbed on silica gel (1 mol%) has been found to be an efficient and recyclable heterogeneous catalyst for rapid conjugate addition of primary and secondary amines with 1,4-naphthoquinone to afford 2-amino-1,4-naphthoquinones under ultrasonication in moderate to high yields without using any solvent. The compounds tested for in vitro antimicrobial activity have shown high antibacterial activity against Gram positive bacteria Bacillus subtilis, Micrococcus luteus, Staphylococcus aureus as compared to Gram negative bacteria Burkholderia cepacia, Escherichia coli, Enterobacter cloacae, Klebseilla pneumoniae and Pseudomonas aeruginosa. High antifungal activity has been observed against Candida albicans and Issatchenkia orientalis for all the compounds.
Photo-oxidation of 2-methylamino-3-(1-piperidinylmethyl)-1,4-naphthoquinone
Ohta,Hinata,Kawasaki,Yamashita
, p. 2360 - 2362 (2007/10/02)
2-Methylamino-3-(1-piperidinylmethyl)-1,4 (7) was prepared via several steps from 2-methyl-1,4-naphthoquinone (vitamin K3 3). The quinone (7) was photochemically oxidized to 2-methylamino-3-(1-piperidinylcarbonyl)-1,3-naphthoquinone (8) and/or 2-alkoxycarbonyl-3-methylamino-1,4-naphthoquinone (9), depending on the solvent used.
One-step synthesis of 1,2,3,4-tetrahydrobenzo[g]quinazoline-5,10-dione derivatives from vitamin K3
Ohta,Hinata,Yamashita,Kawasaki,Jinda,Horie
, p. 1730 - 1735 (2007/10/02)
The reactions of 2-halogenonaphthoquinones (5, 13, 14 and 15) and 2-methyl-1,4-naphthoquinone (20; vitamin K3) with primary and secondary amines were examined. 1,3-Dialkyl-1,2,3,4-tetrahydrobenzo[g]quinazoline-5,10-diones (9) were obtained in moderate yields by treating 20 with formaldehyde in primary amines. A plausible reaction path-way is also presented.
