Category: 95211-67-9

2-(Diethylamino)thieno[1,3]oxazin-4-ones as Stable Inhibitors of Human Leukocyte Elastase was written by Guetschow, Michael;Kuerschner, Lars;Neumann, Ulf;Pietsch, Markus;Loeser, Reik;Koglin, Norman;Eger, Kurt. And the article was included in Journal of Medicinal Chemistry in 1999.Reference of 95211-67-9 The following contents are mentioned in the article:

A series of 2-(diethylamino)thieno[1,3]oxazin-4-ones was synthesized and evaluated in vitro for inhibitory activity toward human leukocyte elastase (HLE). The Gewald thiophene synthesis was utilized to obtain several 2-aminothiophene-3-carboxylates. These precursors were subjected to a 5-step route to obtain thieno[2,3-d][1,3]oxazin-4-ones bearing various substituents at positions 5 and 6. Both thieno[2,3-d]- and thieno[3,2-d]-fused oxazin-4-ones possess extraordinary chem. stability, which was expressed as rate constants of the alk. hydrolysis. The kinetic parameters of the HLE inhibition were determined The most potent compound, 2-(diethylamino)-4H-[1]benzothieno[2,3-d][1,3]oxazin-4-one, exhibited a K_i value of 5.8 nM. 2-(Diethylamino)thieno[1,3]oxazin-4-ones act as acyl-enzyme inhibitors of HLE, similar to the inhibition of serine proteases by 4H-3,1-benzoxazin-4-ones. The isosteric benzene-thiophene replacement accounts for an enhanced stability of the acyl-enzyme intermediates. This study involved multiple reactions and reactants, such as Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (cas: 95211-67-9Reference of 95211-67-9).

Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (cas: 95211-67-9) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, sertaconazole, and also BTCP.Reference of 95211-67-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Thieno[2.3-d]-4-pyrimidones: synthesis, structure and pharmacological properties was written by Perrissin, Monique;Favre, Marylene;Luu-Duc, Cuong;Bakri-Logeais, Francoise;Huguet, Francois;Narcisse, Guy. And the article was included in European Journal of Medicinal Chemistry in 1984.Safety of Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate The following contents are mentioned in the article:

The cyclization of 2-aminothiophenes I [R = CO₂Et; R¹ = Ph, R² = H; R¹R² = (CH₂)₃, (CH₂)₄, CHMe(CH₂)₃, CH₂CHMeCH₂CH₂, CH₂CH₂CHMeCH₂, (CH₂)₅] with HCONH₂ or PhCN yields 4-pyrimidones II (R³ = H, Ph). Similar reaction of I (R = CONH₂) with (MeCO)₂CH₂ gave II (R³ = Me). Their structure and their lactam-lactim tautomerism were investigated by IR spectroscopy. Ten II have analgesic activity equal or superior to that of aspirin. Only II [R¹R² = (CH₂)₃, CH₂CHMeCH₂CH₂, R³ = H] have some antiinflammatory activity. This study involved multiple reactions and reactants, such as Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (cas: 95211-67-9Safety of Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate).

Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (cas: 95211-67-9) belongs to benzothiophene derivatives. Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. It has been used as a raw material for the synthesis of biologically active structures and is found in pharmaceuticals such as leukotriene synthesis inhibitors and antifungals, as well as in many natural products.Safety of Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Design, synthesis, biological evaluation and X-ray crystal structure of novel classical 6,5,6-tricyclic benzo[4,5]thieno[2,3-d]pyrimidines as dual thymidylate synthase and dihydrofolate reductase inhibitors was written by Zhang, Xin;Zhou, Xilin;Kisliuk, Roy L.;Piraino, Jennifer;Cody, Vivian;Gangjee, Aleem. And the article was included in Bioorganic & Medicinal Chemistry in 2011.Formula: C12H17NO2S The following contents are mentioned in the article:

Classical antifolates (4-7) with a tricyclic benzo[4,5]thieno[2,3-d]pyrimidine scaffold and a flexible and rigid benzoylglutamate were synthesized as dual thymidylate synthase (TS) and dihydrofolate reductase (DHFR) inhibitors. Oxidative aromatization of Et 2-amino-4-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate (±)-9 to Et 2-amino-4-methyl-1-benzothiophene-3-carboxylate 10 with 10% Pd/C was a key synthetic step. Compounds with 2-CH₃ substituents inhibited human (h) TS (IC₅₀ = 0.26-0.8 μM), but not hDHFR. Substitution of the 2-CH₃ with a 2-NH₂ increases hTS inhibition by more than 10-fold and also affords excellent hDHFR inhibition (IC₅₀ = 0.09-0.1 μM). This study shows that the tricyclic benzo[4,5]thieno[2,3-d]pyrimidine scaffold is highly conducive to single hTS or dual hTS-hDHFR inhibition depending on the 2-position substituents. The X-ray crystal structures of 6 and 7 (I) with hDHFR reveal, for the first time, that tricyclics 6 and 7 bind with the benzo[4,5]thieno[2,3-d]pyrimidine ring in the folate binding mode with the thieno S mimicking the 4-amino of methotrexate. This study involved multiple reactions and reactants, such as Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (cas: 95211-67-9Formula: C12H17NO2S).

Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (cas: 95211-67-9) belongs to benzothiophene derivatives. Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP.Formula: C12H17NO2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis, Cytotoxic Activity and Molecular Docking Studies of New Condensed Thieno[2,3-d]Pyrimidines as Antitumor Agents was written by Kaliraj, S.;Jeyalakshmi, R.;Kathiravan, M. K.. And the article was included in Pharmaceutical Chemistry Journal in 2020.Reference of 95211-67-9 The following contents are mentioned in the article:

A series of lactam fused thienopyrimidines I [R¹ = H, Me, Et, CO₂Me, etc.; R² = H, Me; R¹R² = (CH₂)₄, (CH₂)₃CH(Me); n = 1, 2, 3] and triazole fused thienopyrimidines II [R¹ = H, Me, CO₂Et, etc.; R² = H, Me, Ph; R³ = Me, 4-OHC₆H₄; R¹R² = (CH₂)₃, (CH₂)₄, (CH₂)₃CH(Me)] were synthesized. The target compounds were obtained in good yield and confirmed for their structural integrity. The cytotoxic activity against A431 human epidermoid carcinoma and H9c2 rat cardiomyocyte cells were studied by MTT assay. Most of the synthesized compounds showed 85% cell death in both human A341 and rat H9c2 cell lines, indicating potential anticancer activity of these compounds Interestingly, compound II [R³ = 4-OHC₆H₄] showed a reversal in trend by enhancing the growth of both A341 and H9c2 cells. This study involved multiple reactions and reactants, such as Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (cas: 95211-67-9Reference of 95211-67-9).

Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (cas: 95211-67-9) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP.Reference of 95211-67-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Enterovirus inhibitory activity of C-8-tert-butyl substituted 4-aryl-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidin-5(4H)-ones was written by Kumar Biswas, Bishyajit;Malpani, Yashwardhan R.;Ha, Neul;Kwon, Do-Hyun;Shin, Jin Soo;Kim, Hae-Soo;Kim, Chonsaeng;Han, Soo Bong;Lee, Chong-Kyo;Jung, Young-Sik. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Safety of Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate The following contents are mentioned in the article:

Members of a series of 4-aryl-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidin-5(4H)-ones were prepared and tested against representative enteroviruses including Human Coxsackievirus B1 (Cox B1), Human Coxsackievirus B3 (Cox B3), human Poliovirus 3 (PV3), human Rhinovirus 14 (HRV14), human Rhinovirus 21 (HRV21) and human Rhinovirus 71 (HRV71). The C-8-tert-Bu group on the tetrahydrobenzene ring in these substances is crucial for their enterovirus activity. One member of this group, 8-(tert-butyl)-4-phenyl-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidin-5(4H)-one , showed single digit micromolar activities (1.6-8.85 μM) against a spectrum of viruses screened, and the highest selectivity index (SI) values for Cox B1 (>11.2), for Cox B3 (>11.5), and for PV3 (>51.2), resp. In contrast, 8-(tert-butyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e][1,2,4]triazolo[4,3a]pyrimidin-5(4H)-one, was the most active analog against the selected HRVs (1.8-2.6 μM), and showed the highest selectivity indexes among the group of compounds tested. The SI values for 8-(tert-butyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e][1,2,4]triazolo[4,3a]pyrimidin-5(4H)-one were 11.5 for HRV14, 8.4 for HRV21, and 12.1 for HRV71, resp. This study involved multiple reactions and reactants, such as Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (cas: 95211-67-9Safety of Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate).

Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (cas: 95211-67-9) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Safety of Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem