31183-89-8

Upstream product

• 23474-98-8 2-amino-5-chlorobenzenethiol 
• 95-24-9 6-chloro-2-aminobenzothiazole 
• 106-47-8 4-chloro-aniline 
• 823-86-9 N-(4-chlorophenyl)hydroxylamine 
• 2942-10-1 6-chloro-1,3-benzothiazole 

Downstream Products

• 155908-74-0 bis(5-chloro-2-N-pyrrolylphenyl)disulfide 
• 155908-92-2 3-chloro-6-phenylpyrrolo<2,1-d><1,5>benzothiazepin-7(6H)-one 
• 155908-83-1 α-<<5-chloro-2-(1H-pyrrol-1-yl)phenyl>thio>phenylacetic acid 
• 155908-93-3 3-chloro-6-(p-methoxyphenyl)pyrrolo<2,1-d><1,5>benzothiazepin-7(6H)-one 
• 155908-84-2 (5-Chloro-2-pyrrol-1-yl-phenylsulfanyl)-(4-methoxy-phenyl)-acetic acid 
• 155908-78-4 (5-Chloro-2-pyrrol-1-yl-phenylsulfanyl)-(4-methoxy-phenyl)-acetic acid ethyl ester 
• 1160032-81-4 ethyl (E)-3-(4-chloro-2-mercaptophenylamino)acrylate 
• 877603-42-4 6-chloro-2-(4-nitrophenyl)benzo[d]thiazole 
• 133689-15-3 C₁₃H₈ClNOS 
• 1242288-47-6 2-(3-nitrophenyl)-6-chlorobenzothiazole 
• 1242325-38-7 6-chloro-2-(3,4,5-trimethoxyphenyl)benzothiazole 
• 154558-90-4 6-chloro-2-(4-methoxyphenyl)benzo[d]thiazole 
• 1336853-41-8 3-(6-chlorobenzothiazol-2-yl)phenol 
• 77333-64-3 2-(4-bromophenyl)-6-chlorobenzothiazole 

Relevant academic research and scientific papers

Expeditious and Efficient ortho-Selective Trifluoromethane-sulfonylation of Arylhydroxylamines

A metal- and oxidant-free, practical and efficient method for the synthesis of highly versatile and synthetically useful ortho-trifluoromethanesulfonylated anilines from arylhydroxylamines and trifluoromethanesulfinic chloride was developed. This rapid tr

FLUOROALLYLAMINE DERIVATIVE AND USE THEREOF

The present invention relates to a fluoroallylamine derivative and use thereof. In particular, the present invention relates to a compound as shown in Formula I, a prodrug, an isomer, an isotope-labeled compound, a solvate or a pharmaceutically acceptable salt thereof, which has VAP-1/SSAO inhibitory activity, and can be used for treating a disease associated with VAP-1/SSAO overactivity.

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.

Facile synthesis of bioactive 4H-[1,4]-benzothiazines under solvent free conditions

An efficient method for synthesis of 4H-[1,4]-benzothiazines under solvent free conditions has been developed. The oxidative condensation of 2-aminobenzenethiols with β-diketones/β-ketoesters in presence of catalytic amount of hydrazine hydrate yields the 4H-[1,4]-benzothiazines. The reaction is accelerated by microwave irradiation under solvent free conditions in presence of an energy transfer agent DMF to get the product in high yield. The 2-aminobenzenethiazole required for the synthesis of 4H-[1,4]-benzothiazines are also obtained by a new method instead of presently used time consuming and low yielding method. The structure of the synthesized compounds has been characterized by IR, NMR, mass spectral studies and elemental analysis.

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.

NOVEL COMPOUNDS

The invention relates to tricyclic derivatives, and their use in treating diseases and conditions mediated by antagonism of the mGluR5 receptor, in particular substance related disorders. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.

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.

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.

Antitumor benzothiazoles. 26.1 2-(3,4-dimethoxyphenyl)-5- fluorobenzothiazole (GW 610, NSC 721648), a simple fluorinated 2-arylbenzothiazole, shows potent and selective inhibitory activity against lung, colon, and breast cancer cell lines

A series of new 2-phenylbenzothiazoles has been synthesized on the basis of the discovery of the potent and selective in vitro antitumor properties of 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (8n; GW 610, NSC 721648). Synthesis of analogues substituted in the benzothiazole ring was achieved via the reaction of o-aminothiophenol disulfides with substituted benzaldehydes under reducing conditions. Compounds were evaluated in vitro in four human cancer cell lines, and compound 8n was found to possess exquisitely potent antiproliferative activity (GI50 0.1 nM for MCF-7 and MDA 468). Potent and selective activity was also observed in the NCI 60 human cancer cell line panel. Structure-activity relationships established that the compound 8n stands on a pinnacle of potent activity, with most structural variations having a deactivating in vitro effect. Mechanistically, this new series of agents contrasts with the previously reported 2-(4-aminophenyl)benzothiazoles; compound 8n is not reliant on induction of CYP1A1 expression for antitumor activity.

Substituted 1,3,2,4-benzodithiadiazines: Novel derivatives, by-products, and intermediates

The synthesis of the title compounds 1 by 1:1 condensation of Ar-N=S=N=SiMe32 with SCl2 followed by intramolecular ortho-cyclization of each [Ar-N=S=N-S-Cl] intermediate is complicated by further reaction of 1 with SCl2 to give Herz salts 3. With the 2:SCl2 ratio of 2:1, the formation of by-products 3 is reduced and novel compounds 1 are accessible. With ortho-I containing starting material 2j, the parent compound 1s is obtained as the result of an unexpected I, not H, substitution. The rate of the 1 + SCl2 reaction depends upon a substituent's position, and the minor 8-R isomers 1l,p (R=Br, I) are isolated for the first time from mixtures with the major 6-R isomers due to reduced reactivity toward SCl2. The synthesized compounds 1-3 are characterized by multinuclear (including nitrogen) NMR and X-ray crystallography. According to the X-ray diffraction data, 1j (6-Br) and 1k (7-Br) derivatives are planar, whereas 1i (5-Br) and 11 (8-Br) are bent along the S1···N4 line by ～5° and ～4°, respectively, and the 1r (7-OCH3) derivative is planar in contrast to the known 5-OCH3 isomer, which possesses a significantly folded heterocycle. The distortion of the planar geometry of some compounds 1 is interpreted in terms of a pseudo-Jahn-Teller effect as the result of π-highest occupied molecular orbital (HOMO) - σ*-(LUMO) lowest unoccupied molecular orbital + 1 mixing in a planar conformation. The 2p compound is the first structurally defined Ar-N=S=N-SiMe3 azathiene. The compound Ar-N=S=N-S-NH-Ar 6 modeling the aforementioned intermediate has been isolated and structurally characterized. We describe the attempts to synthesize compounds 1 from 2-aminobenzenethiols and (SN)4 and from salts 3 and Me3SiN3, and we discuss the reaction pathways.