101337-92-2

Usage

Uses

Used in Pharmaceutical Industry:
6-CHLORO-5-FLUOROBENZIMIDAZOLE-2-THIOL is used as a key intermediate in the synthesis of medications, leveraging its chemical properties to contribute to the development of new therapeutic agents.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-CHLORO-5-FLUOROBENZIMIDAZOLE-2-THIOL serves as a building block for designing and creating novel compounds with potential pharmaceutical applications, taking advantage of its structural attributes to enhance drug discovery and development processes.
Used in Antimicrobial Applications:
6-CHLORO-5-FLUOROBENZIMIDAZOLE-2-THIOL may be employed as an antimicrobial agent due to its inherent biological activity, which can be harnessed to combat microbial infections.
Used in Antifungal Applications:
Similarly, 6-CHLORO-5-FLUOROBENZIMIDAZOLE-2-THIOL has potential use as an antifungal agent, where its structural features could be utilized to inhibit fungal growth and treat related conditions.

Upstream product

• 367-21-5 3-chloro-4-fluorophenylamine 
• 333-20-0 potassium thioacyanate 
• 154371-25-2 1-(3-chloro-4-fluorophenyl)thiourea 

Downstream Products

• 142335-07-7 2-amino-5-chloro-6-fluorophenyl disulfide 
• 917474-03-4 2-amino-4-chloro-5-fluorobenzenethiol 
• 142335-09-9 methyl 6-chloro-7-fluoro-4H-1,4-benzothiazin-2-carboxylate 1-oxide 
• 142335-11-3 methyl 6-chloro-4-ethyl-7-fluoro1,4-benzothiazine-2-carboxylate 1-oxide 
• 1251838-06-8 N-(5-chloro-6-fluoro-1,3-benzothiazol-2-yl)-1,1'-biphenyl-4-carboxamide 
• 1191403-92-5 C₁₆H₁₃ClFN₃O₃S₂ 
• 1191404-01-9 C₁₄H₁₁ClFN₃O₂S₂ 
• 1233400-97-9 C₂₁H₁₄Cl₂FN₃O₃S₂ 
• 1233400-99-1 C₂₂H₁₇ClFN₃O₄S₂ 
• 1304134-24-4 C₁₉H₁₄Cl₂FN₃O₂S 
• 1304134-26-6 C₂₁H₁₇ClFN₃O₂S 
• 1304134-23-3 C₁₉H₁₄ClFN₄O₄S 
• 1304134-22-2 C₁₉H₁₄ClFN₄O₄S 
• 1304134-20-0 C₂₁H₂₀ClFN₄O₂S 

Relevant academic research and scientific papers

Synthesis and antifungal activity against strains of Candida albicans of 6-fluoro-4(5 or 7)-chloro-2-(difluorobenzoyl)aminobenzothiazoles

A series of 6-fluoro-4-(5 or 7)-chloro-2-(difluorobenzoyl) aminobenzothiazoles 3a-r were prepared to investigate their potential biological activity. In this work, the results of their in vitro antifungal activity against some strains of Candida albicans

Synthesis, characterization and drug-likeness predictions of 1,3-thiazole and benzothiazole derivatives

Heterocyclic compounds bearing nitrogen and sulphur in the main skeleton are reported to be a bioactive group. Thiazole and benzothiazole moieties are biologically significant class of this group. This research focus on the synthesis and characterization of 1,3-thiazole and benzothiazole derivatives. Drug likeness predictions were also undertaken for these newly synthesized compounds.

Synthesis, anti-inflammatory, analgesic, 5-lipoxygenase (5-LOX) inhibition activities, and molecular docking study of 7-substituted coumarin derivatives

In the present study, 7-subsituted coumarin derivatives were synthesized using various aromatic and heterocyclic amines, and evaluated in vivo for anti-inflammatory and analgesic activity, and for ulcerogenic risk. The most active compounds were evaluated in vitro for 5-lipoxygenase (5-LOX) inhibition. Docking study was performed to predict the binding affinity, and orientation at the active site of the enzyme. In vivo anti-inflammatory and analgesic activity, and in vitro 5-LOX enzyme inhibition study revealed that compound 33 and 35 are the most potent compounds in all the screening methods. In vitro kinetic study of 35 showed mixed or non-competitive type of inhibition with 5-LOX enzyme. Presence of [Formula presented]3 group in 35 and [Formula presented] in 33 at C6-position of benzothiazole ring were found very important substitutions for potent activity.

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 activity of 2-amino-4H-pyrimido[2,1-b][1,3] benzothiazole-3-carboxylates

3-Chloro-4-fluoro aniline (1) on reaction with potassium thiocyanate (2) followed by the addition of bromine in acetic acid medium yielded 2-amino 5-chloro-6-fluro[2,1-b][1,3]benzothiazole (3). Compound 3 when treated with β-cyanoester undergoes cycloaddi

Synthesis and in vitro anti-HIV activity of N-1,3-benzo[d]thiazol-2-yl-2- (2-oxo-2H-chromen-4-yl)acetamide derivatives using MTT method

A series of novel N-1,3-benzo[d]thiazol-2-yl-2-(2-oxo-2H-chromen-4-yl) acetamide derivatives has been synthesized. All the newly synthesized compounds were evaluated for their anti-HIV activity using MTT method. Most of these compounds showed moderate to potent activity against wild-type HIV-1 with an EC50 ranging from >7 EC50 [μg/ml] to 50 [μg/ml]. Among them, N-1,3-benzo[d]thiazol-2-yl-2-(2-oxo-2H- chromen-4-yl)acetamide 6v was identified as the most promising compound (EC 50 = 7 μg/ml). Among all the compounds, three compounds 6m, 6v and 6u have been exhibits potent anti-HIV activity against MT-4 cells.

Synthesis and pharmacological screening of novel (2-(4-Methyl-2-oxo-2H- chromen-7-yloxy)-N-(benzo[d]thiazol-2-yl))acetamide derivatives

A new series of 2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-N-(benzo[d]thiazol-2- yl)acetamide derivatives (4a-k) was synthesized and evaluated for their D 2 and 5HT2 antagonistic activity as a measure of atypical antipsychotic property. Compounds (4a-k) were synthesized by refluxing various N-(benzothiazol-2-yl)-2-chloroacetamides substituted derivatives (3a-k) with 7-hydroxy-4 methyl-2H-chromen-2-one (1) in acetonitrile and anhydrous K 2CO3. N-(Benzothiazol-2-yl)-2-chloroacetamides substituted derivatives (3a-k) were prepared from the chloroacetyl chloride with various 2-amino benzothiazole substituted derivatives (2a-k). The synthesized compounds were characterized with the help of spectral and analytical data. Most of these compounds showed dopamine D2 receptor antagonistic activity from moderate to high affinity along with serotonin 5-HT2 receptor blockage activity: a property that has been suggested as necessary for atypicality. The D 2 and 5-HT2 receptor blockage activity was evaluated by inhibition of apomorphine-induced climbing behaviour and 5HTP induced head twitches in mice, respectively.

Synthesis and in vivo diuretic activity of biphenyl benzothiazole-2- carboxamide derivatives

A series of N-{(substituted)1,3-benzothiazol-2-yl}-1,1'-biphenyl-4- carboxamides was synthesized by reaction between biphenyl acid chloride and 2-aminobenzothiazole. The synthesized compounds were screened in vivo for diuretic activity. Among the series, N-(1,3-benzothiazol-2-yl)-1,1'-biphenyl-4- carboxamide (II) was found to be the most promising candidate.

Quinolonecarboxylic Acids. 2. Synthesis and Antibacterial Evaluation of 7-Oxo-2,3-dihydro-7H-pyridobenzothiazine-6-carboxylic Acids

A series of pyridobenzothiazine acid derivatives was synthesized and their in vitro antibacterial activity was evaluated.The 1,4-benzothiazine intermediates, which by Gould-Jacobs quinoline synthesis produced pyridobenzothiazine acids, were prepared by hydrolytic basic cleavage of substituted 2-aminobenzothiazoles and successive cyclocondensation with 1-bromo-2-chloroethane or alternatively with monochloroacetic acid, hence reduction by LiAlH4.The pyridobenzothiazine acids 10c, 30, and 31 show potent antibacterial activities against Gram-positive and Gram-negative pathogens.Structure-activity relationships are discussed.The compound 9-fluoro-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyridobenzothiazine-6-carboxylic acid (31) (MF-934) has been found to possess, together with the antibacterial activity, a weak acute toxicity and interesting pharmacokinetic characteristics in several animal species (rat, dog, monkey, man).

Derivatives of pyrido-benzothiazine with high anti-microbial activity

Pyrido-benzothiazine compounds having anti-microbial activity are prepared by (a) reacting 3-chloro-4-fluoroaniline with potassium thiocyanate and bromine to produce 2-amino-6-fluoro-7-chlorobenzothiazole, (b) reacting 2-amino-6-fluoro-7-chlorobenzothiazole with sodium hydroxide to produce the disulfide of 2-amino-5-fluoro 6-chlorothiophenol, (c) reacting the disulfide with sodium monochloroacetate to produce 7-fluoro-8-chloro-2H-1,4-benzothiazin-3(4H)-one, (d) reducing 7-fluoro-8-chloro-2H-1,4-benzothiazin-3(4H)-one to produce 7-fluoro-8-chloro-3,4-dihydro-2H-1,4-benzothiazone, (e) reacting 7-fluoro-8-chloro-3,4-dihydro-2-H-1,4-benzothiazone with ethyl ethoxymethylenemalonate and cyclyzing the intermediate formed with polyphosphoric acid to produce ethyl 9-fluoro-10-chloro-7-oxo-2,3-dihydro-7H-pyrido[1,2,3 de] [1,4]-benzothiazine-6-carboxylate and (f) hydrolyizing the ethyl carboxylate to produce the corresponding carboxylic acid.