scholarly journals Utilization of protopine and related alkaloids. IX. Formation of 4b,6-epidioxybenzo(c)phenanthridine derivative and its reaction with 2,3-dichloro-5,6-dicyanobenzoquinone.

1975 ◽  
Vol 23 (7) ◽  
pp. 1561-1564 ◽  
Author(s):  
MASAYUKI ONDA ◽  
MITSUYO GOTOH ◽  
JUNKO OKADA
Keyword(s):  
Phenanthridine Derivative

scholarly journals The Phenanthridine-modified Tyrosine Dipeptide

2019 ◽  
Vol 92 (2) ◽  
pp. 249-258
Author(s):  
Antonija Erben ◽  
Josipa Matić ◽  
Nikola Basarić ◽  
Ivo Piantanida
Keyword(s):  
Unnatural Amino Acids ◽  
Thermal Denaturation ◽  
Specific Binding ◽  
Quinone Methide ◽  
Melting Temperatures ◽  
Double Helices ◽  
Fluorescence Titrations ◽  
Alkylate Dna ◽  
Ct Dna ◽  
Phenanthridine Derivative

Dipeptide 4 containing two unnatural amino acids, a modified tyrosine and a phenanthridine derivative, was synthesized. Binding of the dipeptide to a series of polynucleotides including ct-DNA, poly A - poly U, poly (dAdT)2, poly dG - poly dC and poly (dGdC)2 was investigated by thermal denaturation experiments, fluorescence spectroscopy and circular dichroism. Thermal denaturation experiments indicated that dipeptide 4 at pH 5.0, when phenanthridine is protonated, stabilizes ds-DNA, whereas it destabilizes ds-RNA. At pH 7.0, when the phenanthridine is not protonated, effects of 4 to the polynucleotide melting temperatures are negligible. At pH 5.0, dipeptide 4 stabilized DNA double helices, and the changes in the CD spectra suggest different modes of binding to ds-DNA, most likely the intercalation to poly dG- poly dC and non-specific binding in grooves of other DNA polynucleotides. At variance to ds-DNA, addition of 4 destabilized ds-RNA against thermal denaturation and CD results suggest that addition of 4 probably induced dissociation of ds-RNA into ss-RNA strands due to preferred binding to ss-RNA. Thus, 4 is among very rare small molecules that stabilize ds-DNA but destabilize ds-RNA. However, fluorescence titrations with all polynucleotides at both pH values gave similar binding affinity (log Ka ≈ 5), indicating nonselective binding. Preliminary photochemical experiments suggest that dipeptide 4 reacts in the photochemical reaction, which affects polynucleotides chirality, presumably via quinone methide intermediates that alkylate DNA.

Phenanthridines. III. Syntheses of 9-bromophenanthridine and 7-bromophenanthridine by Pschorr reactions with sulphonamides derived from N-p-bromobenzyl- and N-o-bromobenzyl-o-phenylenediamines, and a new route to N-sulphonylcarbazoles

1964 ◽  
Vol 17 (12) ◽  
pp. 1406 ◽  
Author(s):  
JL Huppatz ◽  
WHF Sasse
Keyword(s):  
Sodium Nitrite ◽  
Sulphonic Acid ◽  
High Yields ◽  
Hydrolysis Of ◽  
By Products ◽  
Phenanthridine Derivative

9-Bromophenanthridine (Ic) has been prepared by oxidative hydrolysis of 9-bromo-5-p-toluenesulphonyl-j,8-dihydrophenanthridine (IIc), which is one of the products of the copper-catalysed decomposition of diazotized N-p-bromobenzy1.N-p- toluenesulphonyl-o-phenylenediamine (IIIc). 7-Bromophenanthridine (Ie) was similarly synthesized from N-o-bromobenzyl-N-methanesulphonyl-o-phenylenediamine (IIIe) by way of 9-bromo-5-methanesulphonyl-5,6-dihydrophenanthridine (IIe). The decomposition of diazotized o-bromobenzyl-N-p-toluenesulphonyl-o- phenylenediamine (IIId) did not yield the corresponding phenanthridine derivative (IId). By-products formed in the cyclization of (IIIc) include 2-p-bromobenzylamino-4'-methylbiphenyl (Vc), 4-bromo-2'-p-toluenesulphonamidobiphenyl (VIc), and N-p-bromobenzyl-2-amino-5'-methylbiphenyl-2'-sulphonic acid sultam (IVc). The amine (IIId) gave 2-o-bromobenzylamino-4'-methylbiphenyl (Vd), 2-bromo-2'-p-toluenesulphonamidobiphenyl (VId), N-o-bromobenzyl-2-amino-5'-methylbiphenyl- 2'-sulphonic acid sultam (IVd), and AT-p-toluenesulphonylcarbazole (VIIa). The amine (IIIe) gave also 2-bromo-2'-methanesulphonamidobiphenyl (VIe) and N-methanesulphonylcarbazole (VIIb). The relative yields of these products depend inter alia on the amount of sodium nitrite used during the inverse diazotization prior to the addition of copper. Under the influence of cuprous compounds the 2-amino-2'-bromobiphenyls (VId) and (VIe) are converted in high yields to the carbazoles (VIIa) and (VIIb), respectively.

A New Synthesis of Benzo[c]phenanthridine Derivative

Heterocycles ◽  
1976 ◽  
Vol 4 (9) ◽  
pp. 1497 ◽  
Author(s):  
Hideo Iida ◽  
Kohkichiro Takahashi ◽  
Toyohiko Kikuchi
Keyword(s):  
New Synthesis ◽  
Phenanthridine Derivative

ChemInform Abstract: A NEW SYNTHESIS OF BENZO(C)PHENANTHRIDINE DERIVATIVE

1977 ◽  
Vol 8 (4) ◽  
pp. no-no
Author(s):  
H. IIDA ◽  
K. TAKAHASHI ◽  
T. KIKUCHI
Keyword(s):  
New Synthesis ◽  
Phenanthridine Derivative

Rapid Synthesis of Ismine, a Bioactive Amaryllidaceae Alkaloid

2017 ◽  
Vol 41 (4) ◽  
pp. 202-204 ◽  
Author(s):  
Jing-jing Guo ◽  
Bi-juan Yang ◽  
Chen-xu Jing ◽  
Duo-zhi Chen ◽  
Xiao-jiang Hao
Keyword(s):  
Palladium Catalyst ◽  
Biologically Active ◽  
Rapid Synthesis ◽  
One Pot ◽  
Phenanthridine Derivative

Ismine (6-[2-(methylamino)phenyl]-1,3-benzodioxole-5-methanol, 1), a biologically active alkaloid, has been synthesised by a rapid and simple four-step sequence. This synthesis involved a consecutive aryl–aryl and N–aryl coupling, leading to a phenanthridine derivative in a one-pot sequence, which employed a palladium catalyst and trifurylphosphine as the ligand. This synthesis gave an overall yield of 23%.

scholarly journals Utilization of Protopine and Related Alkaloids. VI. Transformation of Berberine to 10b-Methylhexahydrobenzo [c] phenanthridine Derivative

1973 ◽  
Vol 21 (6) ◽  
pp. 1333-1337 ◽  
Author(s):  
MASAYUKI ONDA ◽  
KUMIKO YUASA ◽  
JUNKO OKADA ◽  
KYOKO KATAOKA ◽  
KAORU ABE
Keyword(s):  
Phenanthridine Derivative

Phenanthridine Derivative Host Heat Shock Cognate 70 Down-Regulators as Porcine Epidemic Diarrhea Virus Inhibitors

2021 ◽  
Vol 84 (4) ◽  
pp. 1175-1184
Author(s):  
Duo-Zhi Chen ◽  
Shi-Rui Fan ◽  
Bi-Juan Yang ◽  
Huo-Chun Yao ◽  
Yi-Ting Wang ◽  
...  
Keyword(s):  
Heat Shock ◽  
Porcine Epidemic Diarrhea Virus ◽  
Diarrhea Virus ◽  
Heat Shock Cognate 70 ◽  
Porcine Epidemic Diarrhea ◽  
Phenanthridine Derivative
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