178804-06-3Relevant articles and documents
Synthesis of 2-(4-aminophenyl)benzothiazoles using MF resin supported H+ under solvent free conditions
Lei, Yingjie,Wu, Xinshi,Zhang, Guochun,Ai, Cuiling
, p. 679 - 682 (2015/05/05)
Abstract A simple and convenient approach to 2-(4-aminophenyl)benzothiazole derivatives by condensation of o-aminothiophenol with (un)substituted p-aminobenzoic acid under the action of melamine formaldehyde resin (MFR) supported sulfuric acid under microwave irradiation (MW) and solvent-free conditions has been developed. Structures of the corresponding products were elucidated by IR, 1H NMR spectra, and elemental analysis. The resin could be easily recovered and reused for subsequent reactions.
An efficient one-pot synthesis of benzothiazolo-4β-anilino- podophyllotoxin congeners: DNA topoisomerase-II inhibition and anticancer activity
Kamal, Ahmed,Kumar, B. Ashwini,Suresh, Paidakula,Shankaraiah, Nagula,Kumar, M. Shiva
scheme or table, p. 350 - 353 (2011/02/27)
An efficient one-pot iodination methodology for the synthesis of benzothiazolo-4β-anilino-podophyllotoxin (5a-h) and benzothiazolo-4β- anilino-4-O-demethylepipodophyllotoxin (6a-h) congeners has been successfully developed by using zirconium tetrachloride
Syntheses and DNA-binding studies of a series of unsymmetrical cyanine dyes: Structural influence on the degree of minor groove binding to natural DNA
Karlsson, H. Jonas,Bergqvist, Mattias H.,Lincoln, Per,Westman, Gunnar
, p. 2369 - 2384 (2007/10/03)
Twelve crescent-shaped unsymmetrical dyes have been synthesized and their interactions with DNA have been investigated by spectroscopic methods. A new facile synthetic route to this type of cyanine dyes has been developed, involving the preparation of 6-substituted 2-thiomethyl-benzothiazoles in good yields. The new dyes are analogues to the minor groove binding unsymmetrical cyanine dye, BEBO, recently reported by us. In this dye, the structure of the known intercalating cyanine dye BO was extended with a 6-methylbenzothiazole substituent. Herein we further investigate the role of the extending benzazole heterocycle, as well as of the pyridine or quinoline moiety of the cyanine chromophore, for the binding mode of these crescent-shaped dyes to calf thymus DNA. Flow LD and CD studies of the 12 dyes show that the extent of minor groove binding to mixed sequence DNA varies significantly between the dyes. We find that hydrophobicity and size are the crucial parameters for recognition of the minor groove. The relatively high fluorescence quantum yield of many of these cyanines bound to DNA, combined with their absorption at long wavelengths, may render them useful in biological applications. In particular, two of the benzoxazole containing dyes BOXTO and 2-BOXTO show a high degree of minor groove binding and quantum yields of 0.52 and 0.32, respectively, when bound to DNA.
2-arylbenzazole compounds
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, (2008/06/13)
There are disclosed herein 2-phenylbenzazole compounds having a 3'-substituent and a 4'-NR2R6 substituent in the phenyl group where R5 and R6 are each hydrogen or alkyl, or where the $'-NR5R6 substituent is N-acyl (or N-benzoyl). There are also disclosed
Antitumor benzothiazoles. 7. Synthesis of 2-(4- acylaminophenyl)benzothiazoles and investigations into the role of acetylation in the antitumor activities of the parent amines
Chua, Mei-Sze,Shi, Dong-Fang,Wrigley, Samantha,Bradshaw, Tracey D.,Hutchinson, Ian,Shaw, P. Nicholas,Barrett, David A.,Stanley, Lesley A.,Stevens, Malcolm F. G.
, p. 381 - 392 (2007/10/03)
2-(4-Aminophenyl)benzothiazoles display potent and selective antitumor activity against inter alia breast, ovarian, colon, and renal cell lines, but their mechanism of action, though yet to be defined, may be novel. Metabolism is suspected to play a central role in the mode of action of these benzothiazoles since drug uptake and biotransformation were observed in sensitive cell lines (e.g., breast MCF-7 and MDA 468 cells) in vitro, whereas insensitive cell lines (e.g., prostate PC 3 cells) showed negligible uptake and biotransformation. N-Acyl derivatives of the arylamines have been synthesized, and in vitro studies confirm N-acetylation and oxidation as the main metabolic transformations of 2-(4-aminophenyl)benzothiazoles. With the predominant process being dictated by the nature of the 3'-substituent. The prototype amine 3 underwent mainly N-acetylation in vitro, while 3'- substituted analogues 4 and 5 were primarily oxidized. N-Acetylation of 4 to 11 exerts a drastic dyschemotherapeutic effect in vitro, but acetylation of the halogeno congeners 5-7 gave acetylamines 12-14 which substantially retain selective antitumor activity. In vivo pharmacokinetic studies in rats confirmed rapid and exclusive N-acetylation of the 3'-methyl analogue 4, but less acetylation with the 3'-chloro analogue 5. Distinct expression patterns of N-acetyltransferase NAT1 and NAT2 have been demonstrated in our panel of cell lines.
Antitumor benzothiazoles. 3. Synthesis of 2-(4- aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo
Shi, Dong-Fang,Bradshaw, Tracey D.,Wrigley, Samantha,McCall, Carol J.,Lelieveld, Peter,Fichtner, Iduna,Stevens, Malcolm F. G.
, p. 3375 - 3384 (2007/10/03)
A new series of 2-(4-aminophenyl)benzothiazoles substituted in the phenyl ring and benzothiazole moiety has been synthesized by simple, high- yielding routes. The parent molecule 5a shows potent inhibitory activity in vitro in the nanomolar range against a panel of human breast cancer cell lines, but is inactive (IC50 > 30 μM) against other cell types: activity against the sensitive breast lines MCF-7 and MDA 468 is characterized by a biphasic dose-response relationship. Structure-activity relationships derived using these cell types has revealed that activity follows the heterocyclic sequence benzothiazole > benzoxazole >> benzimidazole and that 2-(4-aminophenyl)benzothiazoles bearing a 3'-methyl- 9a, 3'-bromo- 9c, 3'- iodo- 9f, and 3'-chloro-substituent 9i are especially potent and their activity extends to ovarian, lung, and renal cell lines. Four compounds have been evaluated in vivo against human mammary carcinoma models in nude mice. Compound 9a showed the most potent growth inhibition against the ER+ (MCF- 7 and BO) and ER- (MT-1 and MT-3) tumors. Our efforts to identify a pharmacological mechanism of action for these intriguing compounds have not, as yet, been successful.
