2591-14-2

Usage

Chemical class

Benzothiazole derivatives

Structure

Consists of a benzothiazole group attached to a 3-chloropropyl group through a sulfur atom

Applications

a. Organic synthesis
b. Material science
c. Pharmaceutical research and development

Building block

Used for the synthesis of various organic compounds and materials with specific properties

Biological activities

Presence of the benzothiazole moiety, which is known for its biological activities and pharmacological properties

Safety precautions

Handle with caution and follow proper safety procedures due to potential health and environmental hazards

Upstream product

• 149-30-4 2-Mercaptobenzothiazole 
• 109-70-6 1.3-chlorobromopropane 
• 627-30-5 1-chloro-3-hydroxypropane 
• 142-28-9 1,3-Dichloropropane 
• 2492-26-4 sodium 2-mercaptobenzothiazole 

Downstream Products

• 1427471-21-3 2-{[3-(3,5-diphenyl-1H-1,2,4-triazol-1-yl)propyl]sulfanyl}-1,3-benzothiazole 
• 1427471-22-4 2-{[3-(3,5-bis(3,5-dinitrophenyl)-1H-1,2,4-triazol-1-yl)propyl]sulfanyl}-1,3-benzothiazole 
• 1427471-23-5 2-{[3-(3,5-bis(3,5-dinitrophenyl)-1H-1,2,4-triazol-1-yl)propyl]sulfanyl}-1,3-benzothiazole 
• 1427471-24-6 2-({3-[3,5-bis(2,4-dichlorophenyl)-1H-1,2,4-triazol-1-yl]propyl}sulfanyl)-1,3-benzothiazole 
• 1427471-25-7 2-{[3-(3,5-di(phenoxymethyl)-1H-1,2,4-triazol-1-yl)propyl]sulfanyl}-1,3-benzothiazole 
• 1427471-28-0 2-({3-[3,5-bis(4-chlorophenoxymethyl)-1H-1,2,4-triazol-1-yl]propyl}sulfanyl)-1,3-benzothiazole 
• 1165930-87-9 6-[3-(benzothiazol-2-ylthio)propoxy]-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine 
• 1165930-99-3 6-[3-(benzothiazol-2-ylthio)propoxy]-7-methoxy-N-(4-methylphenyl)quinazolin-4-amine 
• 1165930-96-0 6-[3-(benzothiazol-2-ylthio)propoxy]-7-methoxy-N-(4-methoxyphenyl)quinazoline-4-amine 
• 1165930-93-7 6-[3-(benzothiazol-2-ylthio)propoxy]-N-(4-bromo-2-ethylphenyl)-7-methoxyquinazolin-4-amine 
• 1165930-90-4 6-[3-(benzothiazol-2-ylthio)propoxy]-7-methoxy-N-[3-(trifluoromethyl)phenyl]quinazolin-4-amine 

Relevant academic research and scientific papers

Novel imidazole derivatives as heme oxygenase-1 (HO-1) and heme oxygenase-2 (HO-2) inhibitors and their cytotoxic activity in human-derived cancer cell lines

Heme oxygenase (HO) is a cytoprotective enzyme that can be overexpressed in some pathological conditions, including certain cancers. In this work, novel imidazole derivatives were designed and synthesized as inhibitors of heme oxygenase-1 (HO-1) and heme

Synthesis of novel tetrazole derivatives and evaluation of their antifungal activity

With the appearance of the antifungal resistance, novel antifungal agents need to be identified. In this context new 2,5-disubstituted tetrazole derivatives containing benzothiazole, benzoxazole or phenylsulfonyl moiety were synthesized by N-alkylation of

One-Pot Substitution of Aliphatic Alcohols Mediated by Sulfuryl Fluoride

The Mitsunobu reaction is a powerful transformation for the one-pot activation and substitution of aliphatic alcohols. Significant efforts have focused on modifying the classic conditions to overcome problems associated with purification from phosphine-based byproducts. Herein, we report a phosphine free method for alcohol activation and substitution that is mediated by sulfuryl fluoride. This new method is effective for a wide range of primary alcohols using phthalimide, di-tert-butyl-iminodicarboxylate, and aromatic thiol nucleophiles in 74 % average yield. Activated carbon nucleophiles and a deactivated phenol were also effective for this reaction in good yields. Secondary alcohols were also successful substrates using aryl thiols, affording the corresponding sulfides in 56 % average yield with enantiomeric ratios up to 99:1. This new protocol has a distinct synthetic advantage over many existing phosphine-based methods as the byproducts are readily separable. This feature was exploited in several examples that did not require chromatography for purification. Furthermore, the mild reaction conditions enabled further in situ derivatization for the one-pot conversion of alcohols to amines or sulfones. This method also provides a boarder nucleophile scope compared to existing phosphine-free methods.

A Practical Access to Functionalized Alkyl Sulfinates

We describe herein a three-step synthesis of aliphatic sulfinates. This cost-effective method involves the use of 2-mercaptobenzothiazole under mild conditions and exhibits good yields (up to 78% over three steps). This approach provides an access to a wi

Synthesis and biological evaluation of some novel 3,5-disubstituted-1,2,4- triazole incorporated 2-mercaptobenzothiazoles

Several 2-mercaptobenzothiazole derivatives 5a-i containing 1,2,4-triazole moiety incorporating two additional substituents were synthesized. All the newly synthesized compounds were tested for in vitro activity against certain strains of bacteria such as Enterococcus faecalis, Bacillus coagulans, Pseudomonas aeruginosa, Escherichia coli and Candida albicans. Compound 5a showed significant activity against the Gram-negative bacteria Escherichia coli. Compounds 5a-i were also screened for their antifungal activity against Candida albicans and compounds 5a, 5b, 5d and 5g displayed significant activity against this fungus. Some of these compounds were evaluated for their in vivo anti-inflammatory activity, acute toxicity and ulcerogenic actions. Tested compounds 5g and 5h showed significant anti-inflammatory activity and significant gastrointestinal protection compared to the standard drug diclofenac sodium. Molecular modeling studies of the synthesized compounds are presented.

Synthesis and in vitro antitumor activities of novel 4-anilinoquinazoline derivatives

A series of 6, 7-dialkoxy-4-anilinoquinazolines were designed, synthesized by substituting different heterocycles on 6-position and a variety of anilines on 4-position of the quinazoline. These novel quinazoline compounds were screened for their cytotoxic effect on epidermal growth factor receptor overexpressing skin epidermoid carcinoma cell line (A431), by using nonoverexpressing tumor cells as negative control (breast adeno carcinoma cell line MCF-7). 2-Butyl-4-chloro-1-{3-[7-methoxy-4-(3-(trifluoromethyl)phenylamino)quinazolin-6-yloxy]-propyl}-1H-imidazole-5-carboxaldehyde (30) and 2-butyl-4-chloro-1-{3-[4-(3-iodophenyl amino)-7-methoxyquinazolin-6-yloxy]propyl}-1H-imidazole-5-carboxaldehyde (33) were found to be more potent against A431 cell line (IC50 3.5 and 3 μM) and their activities are comparable to gefitinib. Insilico docking experiments with human EGFR Tyrosine kinase domain (PDB id-2gs2) indicated that 33 docks at the same position as that of gefitinib involving Val702, Ala719, Ser696, and Lys721.

Hexitol derivatives having vasodilative activity

Disclosed is a hexitol derivative represented by the formula (I): STR1 wherein Q represents a formula selected from the group consisting of STR2 wherein a represents NH, O or S; each of b, c and d independently represents CH or N; each of R1, R2, R3 and R4 independently represents hydrogen, lower alkyl, trifluoromethyl, aryl, lower alkanoyloxy, amino, lower alkylamino, lower alkanoylamino, lower alkanoyl, aroyl, halogen, nitro, (CH2)m OR 7, (CH2)m SR7, (CH2)m CO2 R7 where R7 represents hydrogen or lower alkyl and m represents an integer of 0 to 3; each of R5 and R6 independently represents hydrogen or lower alkyl; U represents >N-- or STR3 W represents a single bond, --O-- or --S--; X represents STR4 wherein each of Y1 and Y2 independently represents hydrogen, lower alkyl, hydroxyl, lower alkanoyloxy, nitrile or phenyl; or Y1 and Y2 are combined together to form oxygen; each of Y3 and Y4 independently represents hydrogen or lower alkyl; and l is an integer of 0 to 6, and where l is an integer of 2 to 6, each STR5 may be the same or different; Z represents hydrogen or nitro; and, n is 2 or 3 or a pharmaceutically acceptable salt thereof. The compounds show prominent coronary vasodilative activities, and are useful in treating angina pectoris and myocardial infarction.