85787-95-7

Usage

Uses

Used in Pharmaceutical Industry:
8H-INDENO[1,2-D][1,3]THIAZOL-2-AMINE is used as a starting material for the synthesis of various derivatives with diverse properties, contributing to the development of new drugs and therapeutic agents. Its unique structure and biological activities make it a promising candidate for drug discovery, where it can be utilized to create compounds with specific therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical sector, 8H-INDENO[1,2-D][1,3]THIAZOL-2-AMINE is used as a precursor for the synthesis of agrochemicals, such as pesticides and herbicides. Its potential biological activities can be harnessed to develop new compounds that are effective in controlling pests and weeds, thereby enhancing crop protection and yield.
Used in Organic Synthesis:
8H-INDENO[1,2-D][1,3]THIAZOL-2-AMINE is used as a valuable building block in organic synthesis for the creation of new materials and compounds. Its unique structure allows for the development of a wide range of derivatives with various applications across different fields, including but not limited to pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C10H8N2S/c11-10-12-9-7-4-2-1-3-6(7)5-8(9)13-10/h1-4H,5H2,(H2,11,12)

Upstream product

• 83-33-0 inden-1-one 
• 17356-08-0 thiourea 
• 1775-27-5 2-bromoindanone 
• 95-13-6 1-indene 
• 1579-14-2 2-chloroindanone 

Relevant academic research and scientific papers

Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)

An efficient procedure for the synthesis of 2-aminothiazoles via DBH-mediated oxidative cyclization of styrenes and thioureas is reported. Various alkenes were successfully transformed to the corresponding 2-aminothiazoles in yields of 10–81% via a two-step one-pot manner using DBH as both the bromine source and oxidant. The method can be readily carried out in gram-scale and successfully applied to the synthesis of anti-inflammatory drug fanetizole using styrene as starting material.

Synthesis and antibacterial screening of novel 2-(4-(aryl) thiazol-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-ethanoisoindole-1,3(2H)-dione derivatives

A series of novel 2-(4-(aryl)thiazol-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-ethanoisoindole-1,3(2H)-dione derivatives were synthesized and evaluated for their antimicrobial activity. The structures of the synthesized derivatives (9a-j) were confirmed by means of IR, 1H-NMR, 13C-NMR and elemental analyses. All the compounds 9a-j showed activity against all microorganisms. Compounds 9a, 9c-d, and 9j exhibit potent antibacterial activity against tested S. pyogenes. Compounds 9c showed higher activity than standards against C. perfringes. 9a-e, 9j and 9i possess good activity against A. tumefacen.

Mechanochemical solid-state synthesis of 2-aminothiazoles, quinoxalines and benzoylbenzofurans from ketones by one-pot sequential acid- and base-mediated reactions

α-Chloroketones-obtained by the atom-economical chlorination of ketones with trichloroisocyanuric acid (TCCA) in the presence of p-TSA under ball-milling conditions-were set up for a sequential base-mediated condensation reaction with thiourea/thiosemicarbazides, o-phenylenediamine and salicylaldehyde to afford 2-aminothiazoles, 2-hydrazinylthiazoles, quinoxalines and benzoylbenzofurans, respectively, in respectable yields. The viability of one-pot sequential acid- and base-mediated reactions in the solid state under ball-milling conditions is thus demonstrated.

Synthesis and Carbonic Anhydrase Inhibition of Novel 2-(4-(Aryl)thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione Derivatives

Carbonic anhydrase (CA, EC 4.2.1.1) is a member of the metalloenzyme family. It catalyzes the rapid conversion of carbon dioxide (CO2) and water to bicarbonate (HCO3 ?) and protons (H+) and also plays an important role in biochemical and physiological processes. In this study, a number of novel 2-(4-(aryl)thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives were synthesized and evaluated for their inhibitory characteristics against the human CA isoenzymes I and II (hCA I and hCA II). The structures of the new molecules 8a–i were confirmed by means of IR, 1H NMR, 13C NMR, and elemental analysis. These compounds exhibited excellent inhibitory effects, in the low nanomolar range, with Ki values in the range of 27.07–37.80 nM against hCA I and in the range of 11.80–25.81 nM against hCA II. Our findings suggest that the new isoindolylthiazole derivatives have superior inhibitory effect over acetazolamide (AZA), which is used as clinical CA inhibitor with Ki values of 34.50 and 28.93 nM against the hCA I and hCA II isoenzymes, respectively.

SELECTIVE ACTIVATORS OF THE INTERMEDIATE CONDUCTANCE CA2+-ACTIVATED K+ CHANNEL KCA3.1 AND THEIR METHODS OF USE

Benzoxazole and indole type KCa3.1 activators as well as the therapeutic uses of such compounds in human or animal subjects and their use in ex vivo preservation of organs or tissues.

New positive Ca2+-activated K+ channel gating modulators with selectivity for KCa3.1

Small-conductance (KCa2) and intermediate-conductance (K Ca3.1) calcium-activated K+ channels are voltage-independent and share a common calcium/calmodulin-mediated gating mechanism. Existing positive gating modulators like EBIO, NS309, or SKA-31 activate both KCa2 and KCa3.1 channels with similar potency or, as in the case of CyPPA and NS13001, selectively activate K Ca2.2 and KCa2.3 channels. We performed a structure-activity relationship (SAR) study with the aim of optimizing the benzothiazole pharmacophore of SKA-31 toward KCa3.1 selectivity. We identified SKA-111 (5-methylnaphtho[1,2-d]thiazol-2-amine), which displays 123-fold selectivity for KCa3.1 (EC50 111 ± 27 nM) over KCa2.3 (EC50 13.7 ± 6.9 μM), and SKA-121 (5-methylnaphtho [2,1-d]oxazol-2-amine), which displays 41-fold selectivity for KCa3.1 (EC50 109 nM ± 14 nM) over KCa2.3 (EC50 4.4 ± 1.6 μM). Both compounds are 200- to 400-fold selective over representative KV (KV1.3, KV2.1, KV3.1, and KV11.1), NaV (NaV1.2, NaV1.4, NaV 1.5, and NaV 1.7), as well as CaV1.2 channels. SKA-121 is a typical positive-gating modulator and shifts the calcium-concentration response curve of KCa3.1 to the left. In blood pressure telemetry experiments, SKA-121 (100 mg/kg i.p.) significantly lowered mean arterial blood pressure in normotensive and hypertensive wild-type but not in KCa3.1-/- mice. SKA-111, which was found in pharmacokinetic experiments to have a much longer half-life and to be much more brain penetrant than SKA-121, not only lowered blood pressure but also drastically reduced heart rate, presumably through cardiac and neuronal KCa2 activation when dosed at 100 mg/kg. In conclusion, with SKA-121, we generated a KCa3.1-specific positive gating modulator suitable for further exploring the therapeutical potential of KCa3.1 activation. Copyright

Substituted N-acyl-2-aminothiazoles

There are presented compounds of the formula or a pharmaceutically acceptable salt thereof, which are useful in the treatment of diabetes, diabetic retinopathy, asthma and diarrhea.

New thiazole derivatives as potent and selective 5-hydroxytriptamine 3 (5-HT3) receptor agonists for the treatment of constipation

The syntheses and biological evaluation of a series of novel indeno[1,2-d]thiazole derivatives are described. Several groups reported 5-HT3 receptor agonists which were mainly evaluated for their activities on the von Bezold-Jarisch reflex (B-J reflex). We discovered that tetrahydrothiazolopyridine derivative 1b had a contractile effect on the isolated guinea pig colon with weak B-J reflex. Our efforts to find a new type of 5-HT3 receptor agonists on the isolated guinea pig colon focused on the synthesis of a fused thiazole derivative 1d modified from 1b and reverse-fused thiazole derivatives (7-10). In this series, 10f (YM-31636) showed high affinity and selectivity for the cloned human 5-HT3 receptor; furthermore, it showed potent and selective 5-HT3 receptor agonistic activity. YM-31636 was examined for its effects on defecation in animals, thus evaluating the compound as an agent against constipation.