63755-07-7

Upstream product

• 20358-07-0 2-amino-5-fluorobenzothiazole 
• 371-40-4 4-fluoroaniline 
• 348-40-3 2-amino-6-fluoro-1,3-benzothiazole 

Downstream Products

• 872726-53-9 2-(3,4-dimethoxyphenyl)-6-fluorobenzo[d]thiazole 
• 916606-27-4 6-fluoro-2-(4-hydroxy-3-methoxyphenyl)benzothiazole 
• 916606-28-5 6-fluoro-2-(3-hydroxy-4-methoxyphenyl)benzothiazole 
• 916606-30-9 6-fluoro-2-(5-hydroxy-3,4-dimethoxyphenyl)benzothiazole 
• 916606-31-0 6-fluoro-2-(4-hydroxy-3,5-dimethoxyphenyl)benzothiazole 
• 118220-71-6 6-fluorobenzothiazole 
• 1239726-03-4 6-fluoro-2-(3-fluorophenyl)benzothiazole 
• 1239739-63-9 6-fluoro-2-(3-methoxyphenyl)benzothiazole 
• 1336853-29-2 3-(6-fluorobenzothiazol-2-yl)phenol 
• 1239757-47-1 2-(3-chlorophenyl)-6-fluorobenzothiazole 
• 1263798-58-8 C₁₁H₁₄FNO₂S 
• 1263798-34-0 C₉H₉FN₂S 
• 880088-32-4 6-fluoro-2-(4-hydroxyphenyl)benzothiazole 
• 328087-15-6 4-(6-fluorobenzo[d]thiazol-2-yl)benzenamine 

Relevant academic research and scientific papers

Fluorescence properties of 5-(5,6-dimethoxybenzothiazol-2-yl)-2′- deoxyuridine (dbtU) and oligodeoxyribonucleotides containing d btU

We describe the synthesis and photophysical properties of 11 substituted 5-(benzothiazol-2-yl)-2′-deoxyuridine derivatives and oligodeoxyribonucleotides (ODNs) containing 5-(5,6-dimethoxybenzothiazol-2-yl)- 2′-deoxyuridine (dbtU), which was the strongest fluorescent derivative among those prepared. The fluorescence properties of dbtU itself and ODNs containing dbtU show the same tendency of being weaker in both neutral and acidic solution and stronger in basic solution. The ODNs (15mer) containing 16 combinations of 5′-XbtU-3′ and 5′-btUY-3′, where X, Y = A, T, G, or C, were synthesized, and their fluorescence intensity and quantum yield in basic solution were compared. On average, only the ODN with the 5′-G btU-3′ sequence shows a 7.9-fold lower fluorescence intensity than the other sequences. Ab initio calculations of 5′-G btU-3′ and 5′-btUG-3′ as models under basic conditions suggest that the lower fluorescence of the ODN containing the 5′-GbtU-3′ sequence is caused by a wider overlap between stacked guanine (Gua) and btUra than that of the 5′- btUG-3′ sequence and that the HOMO is delocalized not only on btUra but also on Gua.

A simple and efficient method for synthesis of benzothiazepine derivatives

A series of 1, 5-benzothiazepines were synthesized using disulfides and α, β-unsaturated carbonyl or nitrile compounds as reaction substrates. After reductive cleavage of the S-S bond of disulfides, the resulting thiols were reacted with α,β-unsaturated carbonyl or nitrile compounds to generated seven-membered heterocyclic compounds. In the presence of ammonium thioglycolate, the Michael reaction occurred between disulfides (1) and 4-methyl-3-penten-2-one to give 2, 2, 4-trymethyl-3H-1, 5-benzothiazepine derivatives in good yields. When ethyl acrylate or acrylonitrile was used as the Michael acceptor, 90-99% of (2-amino- phenylsulfanyl)propionitriles (3) and/or 92-99% of (2-amino-phenylsulfanyl) propionic acid ethyl esters (4) were produced. Subsequently, the 1, 5-benzothiazepine compounds 5 and 6 were obtained due to the cyclization reaction. The Japan Institute of Heterocyclic Chemistry.

Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5- fluorobenzothiazole (PMX 610, NSC 721648)

New fluorinated 2-aryl-benzothiazoles, -benzoxazoles, and -chromen-4-ones have been synthesized and their activity against MCF-7 and MDA 468 breast cancer cell lines compared with the potent antitumor benzothiazole 5. Analogues such as 9a,b and 12a,d yielded submicromolar GI50 values in both cell lines; however, none of the new compounds approached 5 in terms of antitumor potency. For 5, binding to the aryl hydrocarbon receptor appeared to be necessary but not sufficient for growth inhibition.

2-arylbenzothiazole analogues and uses thereof

The present invention relates to compounds of the general formula (I) and salts, prodrugs, and stereoisomers thereof, wherein Y independently represents S, O, NR2, SO, SO2; A independently represents a fife- or six-membered aromatic carbocycle or heterocycle and wherein R1 to R20 in formula (I) represent independently of each other a variety of different substituents comprising alkyl, aryl, aralkyl, alkylaryl, heteroaryl groups and monofunctional moieties.

2-Arylbenzothiazole analogues and uses thereof in the treatment of cancer

The present invention relates to anticancer compounds of the general formula (I) and salts and physiologically functional derivatives thereof, wherein Y independently represents S, O, NR 2 , SO, SO 2 ; A independently represents a five- or six-membered aromatic carbocycle or heterocycle and wherein R 1 in formula (I) represents one of the heteroaryl groups defined in the claims.

Synthesis of carbon-11 labeled fluorinated 2-arylbenzothiazoles as novel potential PET cancer imaging agents

Fluorinated 2-arylbenzothiazoles are new potential antitumor drugs, which show potent and selective inhibitory activity against breast, lung, and colon cancer cell lines. Carbon-11 labeled fluorinated 2-arylbenzothiazoles may serve as novel probes for positron emission tomography (PET) to image tyrosine kinase in cancers. The preparation of 4-fluorinated 2-arylbenzothiazoles 4-fluoro-2-(3-benzloxy-4-methoxyphenyl)benzothiazole (6a) and 4-fluoro-2-(3,4-dimethoxyphenyl)benzothiazole (6b) was achieved by a modification of Jacobson thioanilide radical cyclization chemistry. Hydrogenolytic cleavage of the benzyl ether group of compound 6a using H2/Pd-C provided the precursor 4-fluoro-2-(3-hydroxy-4-methoxyphenyl)benzothiazole (7) for radiolabeling. Synthesis of radiolabeling precursors and the reference standards 5- and 6-fluorinated arylbenzothiazoles (11c-n) was achieved via the reaction of o-aminothiophenol disulfides with substituted benzaldehydes under reducing conditions. The target radiotracers carbon-11 labeled 4-, 5-, and 6-fluorinated arylbenzothiazoles (3-[11C]6b, 4-[11C]11c, 3-[11C]11c, 5-[11C]11f, 4-[11C]11f, 4-[11C]11i, 3-[11C]11i, 5-[11C]11l, and 4-[11C]11l) were prepared by O-[11C]methylation of the phenolic hydroxyl precursors (7, 11d, 11e, 11g, 11h, 11j, 11k, 11m, and 11n) with [11C]methyl triflate and isolated by solid-phase extraction (SPE) purification in 30-55% radiochemical yields.

Identification of a novel series of tetrahydrodibenzazocines as inhibitors of 17β-hydroxysteroid dehydrogenase type 3

A novel series of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3) inhibitors has been identified. These inhibitors, based on a dibenzazocine core, exhibited picomolar to low nanomolar inhibition of 17β-HSD3 in cell-free enzymatic as well as in cell-based transcriptional reporter assays.

Substituted 2-arylbenzazole compounds and their use as antitumour agents

Substituted 2-phenylbenzazole compounds of formula (I) wherein X represents S or O and Q represents a direct bond, —CH2— or —CH═Ch—, exhibt selective antiproliferactive activity in respect of mammalian tumour cells. At least in preferred enbodiments the b