Synthesis of the isomeric monomethyl derivatives of the novel naphtho[2′,1′:4,5]thieno[2,3-c]quinoline ring system

1985 ◽  
Vol 22 (1) ◽  
pp. 211-214 ◽  
Author(s):  
Hirotaka Kudo ◽  
Raymond N. Castle ◽  
Milton L. Lee
1980 ◽  
Vol 58 (8) ◽  
pp. 794-802 ◽  
Author(s):  
Marion E. M Baggs ◽  
Brian Gregory

The isothiouronium salt derived from dimethyl 4-chloromethyl-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate reacted with ammonium hydroxide to give dimethyl 7-thia-2-aza-1,3-dimethylbicyclo[3.2.1]oct-3-ene-4,8-dicarboxylate, which could be converted back to a dihydropyridine using iodomethane. Replacement of ammonium hydroxide by sodium hydroxide afforded a tetrahydro- and a dihydrothieno[3,4-c]pyridine as by-products. 3,5-Diacetyl-4-chloromethyl-1,4-dihydro-2,6-dimethylpyridine reacted with thiourea, followed by ammonium hydroxide, to give 3-acetyl-2-methylpyrrole, 4-acetyl- and 4,8-diacetyl-7-thia-2-aza-1,3-dimethylbicyclo[3.2.1]oct-3-ene. The structure and stereochemistry of the novel 7-thia-2-azabicyclo[3.2.1]octenes are established using spectroscopic methods. The mechanism of their formation is discussed in terms of Baldwin's rules.


2005 ◽  
Vol 60 (4) ◽  
pp. 471-475 ◽  
Author(s):  
Barbara Orzeszko ◽  
Tomasz Świtaj ◽  
Anna B. Jakubowska-Mućka ◽  
Witold Lasek ◽  
Andrzej Orzeszko ◽  
...  

Certain adamantylated heterocycles were previously shown to enhance the secretion of tumor necrosis factor alpha (TNF-α) by murine melanoma cells that have been transduced with the gene for human TNF-α and constitutively expressed this cytokine. The stimulatory potency of those compounds depended, among other factors, on the structure of the linker between the adamantyl residue and the heterocyclic core. In the present study, a series of (1-adamantyl)alkylsulfanyl derivatives of heterocyclic compounds was prepared by alkylation of the corresponding thioheterocyles. Of the novel adamantylalkylthio compounds tested in the aforementioned cell line, 2-(2-adamantan-1-ylethylsulfanyl)- 4-methyl-pyrimidine was found to be the most active


Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3268
Author(s):  
Katja S. Håheim ◽  
Emil Lindbäck ◽  
Kah Ni Tan ◽  
Marte Albrigtsen ◽  
Ida T. Urdal Helgeland ◽  
...  

A series of novel quinoline-based tetracyclic ring-systems were synthesized and evaluated in vitro for their antiplasmodial, antiproliferative and antimicrobial activities. The novel hydroiodide salts 10 and 21 showed the most promising antiplasmodial inhibition, with compound 10 displaying higher selectivity than the employed standards. The antiproliferative assay revealed novel pyridophenanthridine 4b to be significantly more active against human prostate cancer (IC50 = 24 nM) than Puromycin (IC50 = 270 nM) and Doxorubicin (IC50 = 830 nM), which are used for clinical treatment. Pyridocarbazoles 9 was also moderately effective against all the employed cancer cell lines and moreover showed excellent biofilm inhibition (9a: MBIC = 100 µM; 9b: MBIC = 100 µM).


2014 ◽  
Vol 70 (9) ◽  
pp. o905-o906 ◽  
Author(s):  
Md. Serajul Haque Faizi ◽  
Ashraf Mashrai ◽  
Saleem Garandal ◽  
M. Shahid

In the title compound, C22H17N3, the dihedral angles between the central benzene ring and the terminal phenyl ring and quinoline ring system (r.m.s. deviation = 0.027 Å) are 44.72 (7) and 9.02 (4)°, respectively, and the bond-angle sum at the amine N atom is 359.9°. In the crystal, the N—H group is not involved in hydrogen bonding and the molecules are linked by weak C—H...π interactions, generating [010] chains.


2013 ◽  
Vol 69 (12) ◽  
pp. o1853-o1854 ◽  
Author(s):  
E. Fazal ◽  
Manpreet Kaur ◽  
B. S. Sudha ◽  
S. Nagarajan ◽  
Jerry P. Jasinski

In the title compound, C18H15NO2, the dihedral angle between the mean planes of the quinoline ring system and the phenyl ring is 48.1 (5)°. The mean plane of the carboxylate group is twisted from the mean planes of the latter by 19.8 (8) and 64.9 (5)°, respectively. The crystal packing features weak C—H...O interactions, which form chains along [010].


1975 ◽  
Vol 28 (6) ◽  
pp. 1249 ◽  
Author(s):  
SE Livingstone ◽  
N Saha

The nickel(II), palladium(II), platinum(II), copper(II), zinc(II) and rhodium(III) chelates of the new fluorinated monothio-β-diketones RC(SH)=CHCOCF3 (R = Pri, Bui) and the iron(III), ruthenium(III) and cobalt(III) chelates of PriC(SH)=CHCOCF3 have been prepared. The mass spectra of all but the two copper chelates have been obtained. The novel features of the spectra are the occurrence of the ions M-(R-H), M-R, and M-LH and the loss of H2S from the ions M-LH and M-L.


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