Category: 15850-81-4

Synthesis of some 4H-pyrimido[2,1-b]benzothiazol-4-ones was written by Alaimo, Robert J.. And the article was included in Journal of Heterocyclic Chemistry in 1973.Category: thiazole The following contents are mentioned in the article:

A series of 8-substituted and 7,8-disubstituted-4-oxo-3-(4H-pyrimido[2,1-b]benzothiazole)carboxylic acids (I) and esters including a 9-aza analog were synthesized from substituted 2-aminobenzothiazoles and di-Et ethoxymethylenemalonate. No significant antiparasitic activity was detected. This study involved multiple reactions and reactants, such as 6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4Category: thiazole).

6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Category: thiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Relation between physiological action and chemical structure. II. Pharmacological studies on various benzothiazole derivatives was written by Fujimura, Hajime. And the article was included in Bulletin of the Institute for Chemical Research, Kyoto University in 1950.Application of 15850-81-4 The following contents are mentioned in the article:

cf. Folia Pharmacol. Japon. 44, 6(1949). The potentiating effects of 2-amino-(I), 2-amino-6-methoxy-(II), 2-amino-6-ethoxy-(III), 2-amino-6-isopropoxy-(IV), 2-(2-diethylaminoethylamino)-6-methoxy-(V), and 2-(2-diethylaminoethylamino)-6-ethoxybenzothiazole (VI) on the hypnotic action of evipan and the analgesic action of morphine were studied. I-VI prolonged the duration of evipan action (30 min. by 50 mg./kg.) in mice 50, 150, 200, 500, 17, and 17%, resp., by injection of 20 mg./kg., 15 min. before the administration of evipan. As determined by Haffner’s method in mice, they did not increase the morphine action (5 mg./kg.). When administered with benadryl (10 mg./kg.), II, III, and IV increased it while I, V, and VI did not. The presence of an alkoxy radical in the 6-position of the benzothiazole ring appears to play an important role in increasing the actions of these 2 drugs, while further substitution of H of the amino radical in the 2-position by the diethylaminoethyl group may result in their inhibition. This study involved multiple reactions and reactants, such as 6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4Application of 15850-81-4).

6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Application of 15850-81-4

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Synthesis of some 4-alkoxy- and 6-alkoxy-2-benzo-thiazolylamides was written by Mndzhoyan, A. L.;Azaryan, A. S.;Iradyan, M. A.;Aroyan, A. A.. And the article was included in Azerbaidzhanskii Khimicheskii Zhurnal in 1967.Application In Synthesis of 6-Isopropoxybenzo[d]thiazol-2-amine The following contents are mentioned in the article:

o- and p-Alkoxynitrobenzenes are hydrogenated over Ni-Cr2O3 to give o- and p-alkoxyanilines (I). Treating I with KSCN and Br gave the corresponding II and III, resp., which were converted into the corresponding amides (IV) and (V), resp. Thus, a mixture of 0.3 mole alkoxynitrobenzene, 50 cc. EtOH, and 4 g. Ni-Cr2O3 catalyst was hydrogenated in an autoclave at 110-20°/100 atm. for 10-12 hrs., filtered, and distilled to give 74.8-86.3% I. From I the following II and III were prepared (R, m.p., m.p. hydrochloride, and % yield given): 6-Et, 159-60°, 199-200°, 60.9; 4-Et, 76-8°, 176-8°, 51.9; 6-Pr, 127-9°, 189-90°, 86.5; 6-iso-Pr, 158-9°, 191-3°, 80.2; 4-Pr, 114-15°, 160-1°, 51.2; 6-Bu, 119-21°, 140-1°, 89.6; 6-iso-Bu, 160-1°, 189-91°, 69.1. A mixture of 0.05 mole acyl chloride and 150 cc. 1:1 Me2CO-dioxane placed in a flask connected with extractor in which a paper extraction shell containing 0.1 mole II or III was placed, was heated on a water bath to complete solution of II or III, filtered, washed with Me2CO, and crystallized from EtOH to obtain the following IV (R, R1, m.p., and % yield given): Et, iso-PrCO, 91-2°, 45.5; Et, Bz, 109-10°, 80.5; Et, MeOC6H4CO (A), 120-2°, 85.3; Et, EtOC6H4CO (B), 116-18°, 76; Et, PrOC6H4CO (C), 94-7°, 84.1; Et, iso-PrOC6H4CO (D), 94-6°, 84.2; Et, BuOC6H4CO (E), 97-8°, 81; Et, PhSO2 (F), 155-7°, 87.4; Et, 2-furoyl (G), 129-30°, 83.3; Et, 2-benzofuroyl (H), 152-4°, 71.8; Et, 2-(2,3-dihydrobenzofuroyl) (I), 110-12°, 70.6; Pr, EtC6H4CO, 191-2°, 79; Pr, G, 224-5°, 80.9; Pr, I, 169-70°, 79.1; and the following V (same data): Et, PrCO, 172-3°, 53.3; Et, iso-PrCO, 140-1°, 45.4; Et, Bz, 222-5°, 87.2; Et, A, 198-200°, 86.9; Et, B, 212-13°, 70.1; Et, C, 224-6°, 84.7; Et, D, 197-200°, 73; Et, F, 199-202°, 60.1; Et, E, 202-3°, 68; Et, iso-BuOC6H4CO, 221-2°, 60; Et, G, 158-9°, 51.9; Et, H, 216-17°, 64.6; Et, I, 142-3°, 90.5; Pr, Bz, 220-2°, 69.2; Pr, A, 145-6°, 80; Pr, B, 204-6°, 86.8; Pr, C, 192-4°, 81.1; Pr, D, 189-90°, 91.8; Pr, E, 197-8°, 67.9; Pr, F, 200-2°, 85.4; Pr, G, 151-2°, 79.5; Pr, H, 212-13°, 65.3; Pr, I, 120-1°, 73.4; iso-Pr, iso-PrCO, 136-9°, 40.3; iso-Pr, BuCO, 138-40°, 49; iso-Pr, Bz, 225-6°, 83.7; iso-Pr, A, 228-9°, 73.1; iso-Pr, B, 215-16°, 60; iso-Pr, F, 255-6°, 68.8; iso-Pr, G, 181-4°, 58.6; Bu, BuCO, 140-1°, 70.6; Bu, Bz, 184-6°, 84.6; Bu, A, 181-2°, 50.1; Bu, B, 182-4°, 81.1; Bu, E, 195-7°, 69.8; Bu, H, 158-60°, 76.5; iso-Bu, A, 222-3°, 85.1; Et, ClCH2CO, 170-1°, 81.4; Bu, ClCH2CO, 172-3°, 70.4. A mixture of 0.03 mole Et2NH, 25 cc. EtOH, 0.01 mole (N-6-alkoxy-2-benzothiazolyl)-2-chloroacetamide, and 25 cc. EtOH was heated on a water bath 2-3 hrs., EtOH was distilled, the residue alkalized with 10% NaHCO3 and extracted with Et2O, the extract dried with Na2SO4 and distilled to give the corresponding V: (R, R1, b.p./mm., m.p., and % yield given): Et, Et2NCH2CO, 218-20°/5, 90-2°, 31.9; Bu, Et2NCH2CO, 130-3°/5, 121-2°, 48.3. This study involved multiple reactions and reactants, such as 6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4Application In Synthesis of 6-Isopropoxybenzo[d]thiazol-2-amine).

6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Application In Synthesis of 6-Isopropoxybenzo[d]thiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

New heterocyclic modifiers of oxidative drug metabolism. I. 6-Substituted-2-aminobenzothiazoles was written by Murray, Michael;Lacey, Ernest;Farrell, Geoffrey C.. And the article was included in Biochemical Pharmacology in 1986.COA of Formula: C10H12N2OS The following contents are mentioned in the article:

A series of 6-substituted-2-aminobenzothiazoles(2-AB) I (R = H, alkoxy, halo, etc.) was synthesized and evaluated as in vitro inhibitors of microsomal mixed-function oxidase  [9038-14-6] activity (as aminopyrine N-demethylase  [9037-69-8]) from phenobarbitone-induced rat liver. Using physiochem. parameters and multiple regression anal., QSAR was derived in which 82% of the data variance was accounted for in terms of the hydrophobic character of the inhibitor and the molar refractivity of the 2-AB 6-substituent. In contrast, literature equations derived from earlier studies with heterocyclic systems possessing nonpolar substituents underestimated by up to an order of magnitude the potency of the present compounds Kinetic studies revealed the 6-n-propoxy-2-AB, one of the more potent compounds, was a pure competitive inhibitor of aminopyrine N-demethylase activity (K_i = 60 μM from Dixon anal.), suggesting the the binding of substrate and inhibitor is mutually exclusive at the cytochrome P 450  [9035-51-2] active site. Binding studies indicated that most 2-AB derivatives elicited mixed-type I-reverse type I optical difference spectra in phenobarbitone-induced microsomes. The overlap of these components resulted in nonlinear double reciprocal plots of the spectral titrations and precluded the determination of binding parameters. In contrast, the more potent inhibitors (the 6-propoxy and 6-butoxy derivatives of 2-AB) were type I ligands with quite high affinity for ferric cytochrome P 450. Although no quant. relationship was apparent between inhibition and spectral binding affinity, a good correlation was observed between inhibition potency (I₅₀) and the capacity of 10 2-AB derivatives to prevent substrate (aminoipyrine) binding to cytochrome P 450. These findings suggest that 2-AB derivatives may inhibit microsomal oxidation via a direct competitive effect on substrate binding to cytochrome P 450. The present study also demonstrates that substitution of heterocyclic systems with hydrophilic groups does not necessarily produce weak inhibitors of mixed-function oxidase activity, and that extrapolation of existing QSAR equations to new inhibitor series must be interpreted with caution. This study involved multiple reactions and reactants, such as 6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4COA of Formula: C10H12N2OS).

6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.COA of Formula: C10H12N2OS

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica