2582-07-2

Usage

Uses

Used in Tire Manufacturing Industry:
Benzothiazol-2-ylguanidine is used as a rubber accelerator for enhancing the vulcanization process, which speeds up the cross-linking of rubber molecules and improves the tensile strength and elasticity of tires.
Used in Industrial Product Manufacturing:
Benzothiazol-2-ylguanidine is also used in the production of various industrial products such as conveyor belts, hoses, and seals, where its vulcanization properties contribute to the durability and performance of these items.
Safety Precautions:
It is important to handle benzothiazol-2-ylguanidine with caution, as it may cause skin and eye irritation. It should be stored and used in accordance with safety guidelines and regulations to ensure the well-being of workers and the environment.

InChI:InChI=1/C8H8N4S/c9-7(10)12-8-11-5-3-1-2-4-6(5)13-8/h1-4H,(H4,9,10,11,12)

Upstream product

• 127099-85-8 N-Cyanoguanidine 
• 137-07-5 2-amino-benzenethiol 
• 136-95-8 2-amino-benzthiazole 
• 867-44-7 S-Methylisothiourea sulfate 
• 420-04-2 CYANAMID 
• 793605-04-6 C₉H₉N₃S₂ 
• 76423-99-9 dimethyl N-(1,3-benzothiazol-2-yl) dithio imidocarbonate 
• 127099-85-8 dicyandiamide 
• 147895-43-0 S-methylisothiourea hemisulphate 

Downstream Products

• 132533-29-0 N⁴-(benzothiazol-2-yl)-N¹-phenylamidinothiourea 
• 380491-63-4 N²-(4-ethyl-5,6,7,8-tetrahydroquinazolin-2-yl)-1,3-benzothiazol-2-amine 
• 573930-39-9 2-(1,3-benzothiazol-2-ylamino)-5-cyano-4-phenylpyrimidine 
• 132533-36-9 N³-Benzothiazol-2-yl-N⁵-phenyl-[1,2,4]thiadiazole-3,5-diamine 
• 1002342-42-8 C₂₇H₂₁FN₄OS 
• 879613-45-3 2-(1,3-benzothiazol-2-ylamino)-5-benzoyl-6-methyl-4-phenyl-1,4-dihydro-pyrimidine 
• 1370024-64-8 N-[(1,3-benzothiazole-2-ylamino)(imino)methyl]-4-nitrobenzenesulfonamide 
• 1649461-62-0 (2Z)-4-amino-2-(1,3-benzothiazol-2-ylimino)-2,5-dihydro-1Himidazole-5-carbonitrile 

Relevant academic research and scientific papers

Boosting the catalytic performance of zinc linked amino acid complex as an eco-friendly for synthesis of novel pyrimidines in aqueous medium

Zinc linked amino acid complex, Zn(l-proline)2, is considered as a green catalyst for the synthesis of novel series of pyrimidine derivatives 5a–q. The pyrimidines 5a–q were prepared via two pathways: the first is a one-pot reaction of guanidines 3a–c with aromatic aldehyde 1 and acetophenones 2; and the second one is the reaction of guanidines 3a–c with different chalcones 4a–j in aqueous medium. The simplicity of the operation, the short reaction time, and the high efficiency (97%) are the main advantages of this protocol. Furthermore, the green aspects of this synthetic protocol were further investigated by examining the reusability of Zn(l-proline)2 complex throughout five consecutive cycles without a significant loss of catalytic activity. This new procedure has presented remarkable advantages in terms of safety, simplicity, stability, mild conditions, a short reaction time, excellent yields, and high purities without using any organic solvents.

Design, synthesis and pharmacological evaluation of pyrimidobenzothiazole-3-carboxylate derivatives as selective L-type calcium channel blockers

L-type voltage gated calcium channels play essential role in contraction of various skeletal and vascular smooth muscles, thereby plays important role in regulating blood pressure. Dihydropyridine receptors have been targeted for development of newer antihypertensive agents, one of the structurally analogs nucleus dihydropyrimidines have been reported earlier by us as a potential agent toward development of calcium channel modulator. A pre-synthetic QSAR was run and on the basis of structure activity relationship a series of twenty three molecules was synthesized and studied by myosin light chain kinase assay (MLCK), Angiotensin Converting Enzyme (ACE) colorimetric assay, non-invasive blood pressure (NIBP) and invasive blood pressure (IBP) methods. Molecules with significant efficacy were studied for their single crystal X-ray diffraction, molecular docking, molecular dynamics and post-synthetic QSAR. The NIBP and IBP methods screened molecules with better percentage inhibition versus time compared to standard drug Nifedipine. The lead compound ethyl 2-methyl-4-(3-nitrophenyl)-4H-pyrimido [2,1-b] [1,3] benzothiazole-3-carboxylate (26) presented a triclinic structure with polymeric chain packing in lattice. 26 exhibited IC50on MLCK assay of 2.1 ± 1.7 μM with selectivity of L-type calcium channels and comparative to Nifedipine. It offered satisfactory physicochemical properties with partition coefficient of (C log P) 4.64. Its pharmacokinetic profile is also good with Cmax at 0.40 μg/ml by oral route with Tmax reaching in 0.5 h which means in 30 min. 26 also exhibits superior t1/2 of 5.4 h and oral bioavailability of (F) 56.75% with an AUC∞ of 0.84 μg h/ml. Molecular docking studies indicates toward the interaction of lead compound via hydrogen bonds with Lys144, Glu181 and Asp183, it forms the Van der Walls interactions with Ser18, Asp20, Asn187, Pro185, Glu180, Glu181 and Arg10 with Glide score and Glide energy to be -3.602 and -47.098, respectively. Post-synthetic QSAR of newly synthesized molecules indicates toward improvement with respect to steric descriptor which contributed negatively in former series.

Direct guanylation of amino groups by cyanamide in water: Catalytic generation and activation of unsubstituted carbodiimide by scandium(iii) triflate

Guanylation proceeded efficiently upon treatment of the various amines with cyanamide in the presence of catalytic amounts of scandium(III) triflate under mild conditions. The method did not require the guanylation reagents to be preactivated, and the reaction proceeded efficiently in water. The method, therefore, has practical utility for substrates that dissolve only in aqueous solutions, for example, peptides or pharmacologically important compounds. Georg Thieme Verlag Stuttgart New York.

Synthesis of pyrimidine, dihydropyrimidinone, and dihydroimidazole derivatives under free solvent conditions and their antibacterial evaluation

The biologically active compounds of pyrimidine, dihydropyrimidinone, and dihydroimidazole have been synthesized in excellent yield under free solvent conditions. The antibacterial evaluation of the products showed a high inhibitory effect. Reaction of 2-guanidinobenzothiazole with several active methylene compounds has revealed formation of the corresponding pyrimidine, dihydropyrimidinone, and dihydroimidazole derivatives under free solvent conditions in very good yield. All compounds have been characterized on the basis of IR, 1H NMR, 13C NMR, mass spectrometry, and X-ray.

A synthetic method to access symmetric and non-symmetric 2-(N,N'-disubstituted)guanidinebenzothiazoles

Symmetric and non-symmetric 2-(N-H, N-methyl, N-ethylenyl and N-aryl)guanidinebenzothiazoles were synthesized from the reaction of ammonia, methylamine, pyrrolidine and aniline with dimethyl benzo[d]thiazol-2-yl- carbonodithioimidate (5) as intermediate. The products were characterized by 1H-, 13C-NMR spectroscopy and three of them by X-ray diffraction analysis. HN-phenyl protons formed intramolecular hydrogen bonds that assist the stereochemistry of the second substituent, whereas the HN-alkyl protons were involved in intermolecular hydrogen bonding.

Synthesis, neurotoxicity and anticonvulsant study of some benzothiazole analogs

A series of benzothiazole sulfonamides, thiosemicarbazones and guanidine derivatives were synthesized by different pathways and tested for the neurotoxicity studies by the Rotarod method. The minimal motor impairment, the significant results were found with compounds (7) and (3). Some of these compounds also showed anticonvulsant activity by decreasing the duration of convulsions in albino mice. Compound (3), (7) and also compound (2) were found to be increased in the onset of convulsion and other test drugs showed moderate protection and animals were recovered in these groups.

COMPOUNDS, COMPOSITIONS AND METHODS OF INHIBITING A-SYNUCLEIN TOXICITY

Compounds and compositions are provided for treatment or amelioration of one or more symptoms of α-synuclein toxicity, α-synuclein mediated diseases or diseases in which α-synuclein fibrils are a symptom or cause of the disease. In one embodiment, the compounds for use in the compositions and methods are heteroaryl acylguanidines, heteroarylhydrazones, dihydropyridones, heteroaryl and aryl styryl ketones, and heteroarylpyrazoles.

Microwave-assisted synthesis of s-triazino[2,1-b][1,3]benzoxazoles, s-triazino[2,1-b][1,3]benzothiazoles, and s-triazino[1,2-a]benzimidazoles

2-Amino-4-oxo-derivatives of s-triazino[2,1e][1,3]benzoxazoles, s-triazino[2,1,b][1,3]benzothiazoles, and s-triazino[1,2-a]benzimidazoles were synthesized by carbonylation of 2-benz-oxazolylguanidines, 2- benzothiazolylguanidines, and 2-benzimidazolylguanidines with phenyl isocyanate under microwave irradiation (180°C, 15 minutes). Using phenyl isothiocyanate instead of phenyl isocyanate under the same conditions led to the successful ring closure via thiocarbonylation of 2-benzoxazolylguanidines. However, the formation of 2-imino-4-phenylimino-s-triazino[2,1-b][1,3]benzothiazoles from 2-benzothiazolylguanidines was observed instead under microwave irradiation conditions. Georg Thieme Verlag Stuttgart.

Three-component synthesis of 4-aryl-5-cyano-2-hetarylaminopyrimidines

Three-component condensation of benzooxazol-2-yl-, benzothiazol-2-yl-, and 5-ethoxycarbonyl-4-methyl-1,3-thiazol-2-ylguanidines with orthoesters and aroylacetonitriles afforded 4-aryl-5-cyano-2-hetarylaminopyrimidines.