- 15N-,13C- and 1H-NMR Spectroscopy characterization and growth inhibitory potency of a combi-molecule synthesized by acetylation of an unstable monoalkyltriazene
-
6-(3-Methyltriaz-1-en-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione referred to as EG22 (8a), is an open-chain 3-alkyl-1,2,3-triazene termed “combi-molecule” designed to inhibit poly(adenosine diphosphate ribose) polymerase (PARP) and damage DNA. To delay its hydrolysis, acetylation of N3 was required. Being a monoalkyl-1,2,3-triazene, EG22 could assume two tautomers in solution or lose nitrogen during the reaction, thereby leading to several acetylated compounds. Instead, one compound was observed and to unequivocally assign its structure, we introduced isotopically labeled reagents in its preparation, with the purpose of incorporating 15N at N2 and 13C in the 3-methyl group. The results showed that the 1,2,3-triazene moiety remained intact, as confirmed by 15N-NMR, coupling patterns between the 15N-labeled N2 and the 13C-labeled methyl group. Furthermore, we undertook heteronuclear single quantum coherence (HSQC) and heteronuclear multiple bond correlation (HMBC) experiments that permitted the detection and assignment of all four nitrogens in 6-(3-acetyl-3-methyltriaz-1-en-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione, referred to as ZSM02 (9a), whose structure was further confirmed by X-ray crystallography. The structure showed a remarkable coplanarity between the N-acetyltriazene and the naphtalimide moiety. Thus, we unequivocally assigned 9a as the product of the reaction and compared its growth inhibitory activity with that of its precursor, EG22. ZSM02 exhibited identical growth inhibitory profile as EG22, suggesting that it may be a prodrug of EG22.
- Mouhri, Zhor Senhaji,Goodfellow, Elliot,Kelley, Steven P.,Stein, Robin S.,Rogers, Robin D,Jean-Claude, Bertrand J
-
-
Read Online
- Synthesis, structural characterization, antibiotics sensing and coordination chemistry of a fluorescent 4-amino-1,8-naphthalimide Tr?ger’s base supramolecular scaffold
-
The solvothermal synthesis and structural characterization of two new supramolecular coordination polymers featuring a unique V-shaped ligand bis-[N-(3-pyridyl)methyl)]-9,18-methano-1,8-naphthalimide-[b,f][1,5]diazocine (TBNap), are reported. The ligand TBNap was synthesized as a racemic mixture and the molecular structure was analyzed crystallographically. TBNap showed a positive solvatochromism effect which was further supported by DFT calculations illustrating the D-π-A type fluorophore effects within the ligand structures. TBNap was further employed as a potential fluorescence probe for the discriminative sensing of structurally assorted antibiotics. A strong fluorescence quenching and preferential binding affinity were realized for nitro-containing antibiotics, i.e., Furazolidone, Nitrofurantoin and Nitrofurazone. The solvothermal reaction of TBNap with Cd(OAc)2?2H2O afforded a one-dimensional coordination polymer (TB-CP-1, poly-[Cd(TBNap)(OAc)2]). Similarly, reaction between TBNap and CdCl2.4H2O in DMF-C2H5OH rendered a 4,4’-2D coordination sheet (TB-CP-2, poly-[CdCl2(TBNap)]·DMF). The extended polymeric structures are further propagated into 3D supramolecular network through multiple face-to-face π-π interaction.
- Lovitt, June I.,Umadevi, Deivasigamani,Raja Lakshmi, Pandi,Twamley, Brendan,Gunnlaugsson, Thorfinnur,Shanmugaraju, Sankarasekaran
-
-
Read Online
- Fluorescent compound used for APN inhibitor and application of fluorescent compound
-
The invention discloses a fluorescent compound used for an APN inhibitor and application of the fluorescent compound. The general molecular formula of the compound is (I) or (II). In the general molecular formula, R1is hydrogen, methyl, ethyl, propyl, butyl, amyl, hexyl, benzyl, 2-amino ethyl, 2, 2-N, N-dimethylethyl or hydroxyl; R2 is hydrogen, halogen or a hydrophilic carboxyl group; and R is methyl or ethyl. The inhibitor can be used as an aminopeptidase N inhibitor, and is used for detecting tissue distribution of aminopeptidase N and cancer cells and Doppler tissue imaging; and the inhibitor can be used as an anti-solid tumor medicine, and is used for detection of abnormal expression of aminopeptidase N and disease diagnosis.
- -
-
Paragraph 0072; 0074; 0075
(2017/08/28)
-
- Visible-light-induced cleavage of 4-α-amino acid substituted naphthalimides and its application in DNA photocleavage
-
A new kind of visible-light photocleavable molecule, 4-α-amino acid substituted naphthalimide, is reported. The cleavage occurred at the C-N bond between the 4-amino and the amino acid residue and released a 4-aminonaphthalimide. A lysine substituted naphthalimide exhibited a strong DNA photocleavage activity when irradiated with a blue light LED. This journal is
- Zhou, Jin,Fang, Canliang,Liu, Ying,Zhao, Yao,Zhang, Nan,Liu, Xiangjun,Wang, Fuyi,Shangguan, Dihua
-
supporting information
p. 3931 - 3935
(2015/03/30)
-
- NUCLEOPHILIC DISPLACEMENT OF THE NITRO GROUP IN 2- AND 4-NITRONAPHTHALIC-1,8-ANHYDRIDES AND THEIR DERIVATIVES
-
The nitro group in 2- and 4-nitronaphthalic-1,8-anhydrides can be substituted by amines in certain cases with retention of the anhydride grouping.
- Alexiou, Michael,Tyman, John,Wilson, Ian
-
p. 2303 - 2306
(2007/10/02)
-
