18378-22-8

Upstream product

• 110-89-4 piperidine 
• 16322-19-3 4-nitro-2,1,3-benzoxadiazole 
• 10199-89-0 NBD chloride 

Relevant academic research and scientific papers

The remarkable effect of 7-amino substituents on the reactivity of 4-nitrobenzofurazans with nucleophiles

The reactions of four 4-nitrobenzofurazans (4a-4d) substituted at the 7 position with (a) N-ethyl, (b) N-butyl, (c) piperidino, or (d) pyrrolidino groups have been examined with sulfite ions and with hydroxide ions in water-DMSO (80:20, v/v). Addition of

4-Amino derivatives of 7-nitro-2,1,3-benzoxadiazole: The effect of the amino moiety on the structure of fluorophores

The crystal structures of three 4-amino derivatives of 7-nitro-2,1,3-benzoxadiazole with increasing substituent ring size, viz, 7-nitro-4-(pyrrolidin-1-yl)-2,1,3-benzoxadiazole, C10H10N4O3, 7-nitro-4-(piperidin-1-yl)-2,1,3-benzoxadiazole, C11H12N4O3, and 4-(azepan-1-yl)-7-nitro-2,1,3-benzoxadiazole, C12H14-N4O3, have been determined in order to understand their photophysical behaviour. All three were found to crystallize in centrosymmetric space groups. There is considerable electron delocalization compared with the parent compound, although the five-membered oxadiazole ring apparently does not participate in this. The length of the C-N bond between the amino N atom and the 7-nitrobenzoxadiazole system is found to be shorter than in similar compounds, as is the C-Nnitro bond. In each structure, the nitro group lies in the plane of the benzoxadiazole unit.

A General Strategy to Enhance Donor-Acceptor Molecules Using Solvent-Excluding Substituents

While organic donor-acceptor (D-A) molecules are widely employed in multiple areas, the application of more D-A molecules could be limited because of an inherent polarity sensitivity that inhibits photochemical processes. Presented here is a facile chemical modification to attenuate solvent-dependent mechanisms of excited-state quenching through addition of a β-carbonyl-based polar substituent. The results reveal a mechanism wherein the β-carbonyl substituent creates a structural buffer between the donor and the surrounding solvent. Through computational and experimental analyses, it is demonstrated that the β-carbonyl simultaneously attenuates two distinct solvent-dependent quenching mechanisms. Using the β-carbonyl substituent, improvements in the photophysical properties of commonly used D-A fluorophores and their enhanced performance in biological imaging are shown.

NBD-organic amine fluorescence probe, and preparation method and application thereof

The invention discloses an NBD-organic amine fluorescence probe, and a preparation method and an application thereof. The structure of the fluorescence probe is represented by formula (1); and in the formula (1), m is 0 or an integer in a range of 1 to 5,

Investigation of thiolysis of NBD amines for the development of H2S probes and evaluating the stability of NBD dyes

In order to evaluate the thiolysis of NBD (7-nitro-1,2,3-benzoxadiazole) amines for development of H2S probes, herein we investigated the reactivity and selectivity of a series of NBD amines for the first time. The piperazinyl- and piperidyl-ba

POTENT ANALOGUES OF THE C-MYC INHIBITOR 10074-G5 WITH IMPROVED CELL PERMEABILITY

The present invention relates compounds and compositions for interfering with the association of Myc and Max. These compounds and compositions are useful in methods for inhibiting growth or proliferation of a cell. Methods of inhibiting growth or proliferation of a cell comprise contacting the cell with an amount of a compound that interferes with Myc and Max association effective to inhibit growth or proliferation of the cell. The compounds exhibit increased inhibitory activity against c-Myc relative to the known c-Myc inhibitor small-molecule benzofurazan N-([1,1′-biphenyl]-2-yl)-7-nitrobenzo[c][1,2,5]oxadiazol-4-amine (10074-G5).

Pharmacophore identification of c-Myc inhibitor 10074-G5

A structure-activity relationship (SAR) study of the c-Myc (Myc) inhibitor 10074-G5 (N-([1,1′-biphenyl]-2-yl)-7-nitrobenzo[c][1,2,5]oxadiazol-4- amine, 1) - which targets a hydrophobic domain of the Myc oncoprotein that is flanked by arginine residues - was executed in order to determine its pharmacophore. Whilst the 7-nitrobenzofurazan was found to be critical for inhibitory activity, the ortho-biphenyl could be replaced with a para-carboxyphenyl group to furnish the new inhibitor JY-3-094 (3q). Around five times as potent as the lead with an IC50 of 33 μM for disruption of the Myc-Max heterodimer, JY-3-094 demonstrated excellent selectivity over Max-Max homodimers, with no apparent effect at 100 μM. Importantly, the carboxylic acid of JY-3-094 improves the physicochemical properties of the lead compound, which will facilitate the incorporation of additional hydrophobicity that might enhance Myc inhibitory activity further still.

Unusual reaction of 4-nitrobenzofurazan with amines

The treatment of 4-nitrobenzofurazan with secondary amines resulted in the formation of 4-amino-5,7-bis(dialkylamino)-benzofurazans, as established by X-ray diffraction analyses; this is the first example of SNH reaction with synchro

Photophysical and dynamic NMR studies on 4-amino-7-nitrobenz-2-oxa-1, 3-diazole derivatives: Elucidation of the nonradiative deactivation pathway

A series of 4-aminonitrobenzoxadiazole (NBD) derivatives in which the amino nitrogen is part of a four- to seven-membered heterocyclic ring and a second series of 4-dialkylamino NBD derivatives with different alkyl chain lengths have been prepared and fully characterized and their photophysical properties investigated in an attempt to find out the nonradiative deactivation pathway of the fluorescent state in these systems. It is observed that the fluorescence properties of the NBD derivatives are highly sensitive to the structure of the amino moiety and the polarity of the surrounding media. It is shown that the nonradiative rate constants for the derivatives with large alkyl groups and large ring systems are considerably higher than those for systems with smaller alkyl groups and smaller ring systems. Dynamic NMR experiments have been carried out to probe the internal motion in the systems. The internal rotation around the bond connecting the amino nitrogen and the NBD ring is found to be rather slow in the ground state. The rate for the internal rotation is found to be the highest for the six-membered ring, and this has been interpreted in terms of the partial double bond character of the C-N bond. The results of the experiments seem to indicate that inversion of the amino nitrogen plays the most important role in determining the fluorescence efficiency of the systems.

Derivatization of Amines with 4-Substituted 7-Nitrobenzofurazans

Electrophilic derivatives of 4-nitro-benzofurazan with different reactivities were used to synthesize 28 new mono- and disubstituted 4-amino-7-nitrobenzofurazans 2b, 2d, 2f-2i, 2l, 2m-2n, 3b-3f, 3h-3j, 4c-4d, 4f-4k, 4m, 4o-4p.A reaction mechanism is proposed on the basis of the differences of the reactivities and a preliminary kinetic examination.The acid character of the N-H-function in monosubstituted compounds is demonstrated by means of spectroscopical investigation of pKa-values.Data from i.r., u.v./vis, and fluorescence studies are offered.