Category: benzothiophene

On March 31, 2011, Pinson, Jo-Anne; Schmidt-Kittler, Oleg; Zhu, Jiuxiang; Jennings, Ian G.; Kinzler, Kenneth W.; Vogelstein, Bert; Chalmers, David K.; Thompson, Philip E. published an article.Related Products of 16296-68-7 The title of the article was Thiazolidinedione-Based PI3Kα Inhibitors: An Analysis of Biochemical and Virtual Screening Methods. And the article contained the following:

A series of synthesized and com. available compounds were assessed against PI3Kα for in vitro inhibitory activity and the results compared to binding calculated in silico. Using published crystal structures of PI3Kγ and PI3Kδ co-crystallized with inhibitors as a template, docking was able to identify the majority of potent inhibitors from a decoy set of 1000 compounds On the other hand, PI3Kα in the apo-form, modeled by induced fit docking, or built as a homol. model gave only poor results. A PI3Kα homol. model derived from a ligand-bound PI3Kδ crystal structure was developed that has a good ability to identify active compounds The docking results identified binding poses for active compounds that differ from those identified to date and can contribute to our understanding of structure-activity relationships for PI3K inhibitors. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Related Products of 16296-68-7

The Article related to structure thiazolidinedione derivative pi3k inhibitor screening preparation, Pharmacology: Structure-Activity and other aspects.Related Products of 16296-68-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On March 10, 2016, Abraham, Rebecca J.; Stevens, Andrew J.; Young, Kelly A.; Russell, Cecilia; Qvist, Anastasia; Khazandi, Manouchehr; Wong, Hui San; Abraham, Sam; Ogunniyi, Abiodun D.; Page, Stephen W.; O’Handley, Ryan; McCluskey, Adam; Trott, Darren J. published an article.Formula: C9H5ClOS The title of the article was Robenidine Analogues as Gram-Positive Antibacterial Agents. And the article contained the following:

Robenidine, (2,2′-bis[(4-chlorophenyl)methylene]carbonimidic dihydrazide) (1), was active against MRSA and VRE with MIC’s of 8.1 and 4.7 μM, resp. SAR revealed tolerance for 4-Cl isosteres, and imine carbon alkylation identified a methyl/ethyl binding pocket that also accommodated a CH2OH moiety. Other analigs were active against 24 clin. MRSA and MSSA isolates, and no dose-limiting cytotoxicity at ≥2× MIC or hemolysis at ≥8× MIC was observed Polymyxin B addition engendered Escherichia coli and Pseudomonas aeruginosa Gram-neg. activity MIC’s of 4.2-21.6 μM. 1 and 75 displayed excellent microsomal stability, intrinsic clearance, and hepatic extraction ratios with T1/2 > 247 min, CLint < 7 μL/min/mg protein, and EH < 0.22 in both human and mouse liposomes for 1 and in human liposomes for I. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Formula: C9H5ClOS

The Article related to robenidine antibacterial bacterial infection, Pharmacology: Structure-Activity and other aspects.Formula: C9H5ClOS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Chapman, Norman Bellamy; Ewing, David F.; Scrowston, R. M.; Westwood, R. published an article in 1968, the title of the article was Proton magnetic resonance spectra of some benzo[b]thiophene derivatives.Formula: C9H5ClOS And the article contains the following content:

Attempts are made to correlate the chem. shifts in the 100 Mc./sec. 1H N.M.R. spectra of 42 benzo[b]thiophene derivatives with the substituents present in the mol., and the relations are rationalized where possible. Coupling constants are also recorded, and their dependence on bond order and on other factors is discussed. The changes in the chem. shifts and coupling constants when the benzo[b]thiophenes are oxidized to the 1,1-dioxides are recorded and discussed. 43 references. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Formula: C9H5ClOS

The Article related to thiophenes nmr benzo, benzothiophenes nmr, nmr benzothiophenes, nmr (nuclear magnetic resonance) and other aspects.Formula: C9H5ClOS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Iddon, B.; Dickinson, R. P. published an article in 1971, the title of the article was Condensed thiophen ring systems. VI. Synthesis and reactions of 5-methyl- and 5-chloro-3-benzo[b]thienyllithium.Category: benzothiophene And the article contains the following content:

Bromination of 5-methyl- and 5-chlorobenzo[b]thiophene in CHCl3 gave 2,3-dibromo-5-methyl-, and a mixture of 20% 3-bromo-5-chloro- and 80% 2,3-dibromo-5-chlorothiophene, resp.; reaction of the 2,3-di-Br derivatives with BuLi-Et2O at 0° gave 3-bromo-5-methyl- (I) and 3-bromo-5-chlorobenzo[b]thien-2-yllithium (II). Reaction of I and II with CO2 gave the corresponding 2-carboxylic acids, and with HCl gave 5-methyl- (III) and 5-chloro-3-bromobenzo[b]thiophene (IV). Reaction of III and IV with BuLi-Et2O at -70° gave 5-methyl- (V) and 5-chlorobenzo[b]thien-3-yllithium (VI), resp. V and VI reacted with CO2, DMF, and Me2SO4 to give the corresponding 3-carboxylic acids, 3-carboxaldehydes, and 3-Me derivatives, resp. Huang-Minlon reduction of 5-methylbenzothio[b]phene-3-carboxaldehyde gave 3,5-dimethylbenzo[b]thiophene. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Category: benzothiophene

5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas:16296-68-7) belongs to benzothiophene. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP. Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

El Shanta, M. S.; Scrowston, R. M. published an article in 1967, the title of the article was Preparation and properties of some 3-acetyl- and 3-formyl-5-halobenzo[b]thiophenes.Name: 5-Chlorobenzo[b]thiophene-3-carbaldehyde And the article contains the following content:

5-Chloro- and 5-bromobenzo[b]thiophene-3-carboxaldehydes (I) (X = Cl and Br) were prepared from the corresponding 3-bromomethyl compound either by the Sommelet reaction (65%) or by the Kroehnke reaction (30% yield). They had the usual properties of an aromatic aldehyde; in particular, they underwent the Doebner reaction with malonic acid, and formed crystalline condensation products with rhodanine. Friedel-Crafts acetylation of 5-chloro- or 5-bromobenzo[b]thiophene gave predominantly the 3-acetyl derivative This reacted with Me2NH.HCl and H2CO (Mannich reaction) to give the corresponding keto amine, the keto group of which was reduced with NaBH4. The resulting alcs. were treated with SOCl2 to give the corresponding substituted 3-chloropropylamines. 34 references. The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Name: 5-Chlorobenzo[b]thiophene-3-carbaldehyde

5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas:16296-68-7) belongs to benzothiophene. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP. Name: 5-Chlorobenzo[b]thiophene-3-carbaldehyde

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On May 9, 2019, Kurz, Guido; Camacho Gomez, Juan published a patent.Synthetic Route of 16296-68-7 The title of the patent was Preparation of novel dihydropyridine derivatives as androgen receptor and glucocorticoid receptor modulators. And the patent contained the following:

The present invention relates to novel dihydropyridine derivatives I [R1 = CN, C(O)NH2, COR5, CO2R5 (wherein R5 = (un)substituted alkyl, cycloalkyl); R2 = CN, COR8, CO2R8, SOnR8, C(O)NR8R9 (n = 1-2; R8 and R9 = (independently) H, (un)substituted alkyl, H, etc.; or R8 and R9 together with the nitrogen atom to which they are attached form (un)substituted 5-6 membered heterocycle which optionally comprises 1 heteroatom selected from O and N); R3 = H, NH2, CN, etc.; R4 = H, CN, (un)substituted alkyl, etc.; X1-X5 = (independently) CB1, N and CH (B1 = halo, CN, (un)substituted 5-6 membered heteroaryl, etc.)] and pharmaceutically acceptable salts thereof, as modulators of nuclear receptors selected from androgen receptor and glucocorticoid receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathol. conditions or diseases that can improve by modulation of androgen receptor and/or glucocorticoid receptor, selected from cancer, metastasizing cancers, benign prostate hyperplasia, polycystic ovary syndrome (PCOS), hair loss, hirsutism, acne, hypogonadism, muscle wasting diseases, cachexia, Cushing’s syndrome, anti-psychotic drug induced weight gain, obesity, post-traumatic stress disorder and alcoholism. Over three-hundred compounds I were prepared For example, heating a mixture of 3-(benzo[b]thiophen-3-ylmethylene)pentane-2,4-dione, Me 3-oxobutanoate and 30% aqueous ammonium in iso-PrOH at reflux temperature for 12 h afforded 25% II (both enantiomers were separated). Exemplified compounds I were evaluated for their androgen receptor and glucocorticoid receptor modulatory activities (data given for representative compounds I). The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Synthetic Route of 16296-68-7

The Article related to pyridine dihydropyridine preparation nuclear androgen glucocorticoid receptor modulator antitumor, benign prostate hyperplasia polycystic ovary syndrome treatment dihydropyridine preparation, hair loss hirsutism acne hypogonadism treatment dihydropyridine pyridine preparation and other aspects.Synthetic Route of 16296-68-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

On May 8, 2019, Kurz, Guido; Camacho Gomez, Juan published a patent.Application In Synthesis of 5-Chlorobenzo[b]thiophene-3-carbaldehyde The title of the patent was Preparation of novel dihydropyridine derivatives as androgen receptor and glucocorticoid receptor modulators. And the patent contained the following:

The present invention relates to novel dihydropyridine derivatives I [R1 = CN, CHO, COR5, CO2R5 (wherein R5 = (un)substituted alkyl, cycloalkyl); R2 = CN, COR8, CO2R8, SOnR8, C(O)NR8R9 (n = 1-2; R8 and R9 = (independently) H, (un)substituted alkyl, cycloalkyl, etc.; or R8 and R9 together with the nitrogen atom to which they are attached form (un)substituted 5-6 membered heterocycle which optionally comprises 1 heteroatom selected from O and N); R3 = H, NH2, CN, etc.; R4 = H, CN, (un)substituted alkyl, etc.; or R1 and R3 or R2 and R4 form together (CR10R11)n (n = 3-4 wherein 1, 2 or 3 of CR10R11 moieties may be independently replaced by a group selected from O, S, C(O) and (un)substituted NH; R10, R11 = (independently) H, (un)substituted Ph or 5-6 membered heteroaryl, etc.); X1-X5 = (independently) CB1, N and CH (B1 = halo, CN, (un)substituted 5-6 membered heteroaryl, etc.)] and pharmaceutically acceptable salts thereof, as modulators of nuclear receptors selected from androgen receptor and glucocorticoid receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathol. conditions or diseases that can improve by modulation of androgen receptor and/or glucocorticoid receptor, selected from cancer, metastasizing cancers, benign prostate hyperplasia, polycystic ovary syndrome (PCOS), hair loss, hirsutism, acne, hypogonadism, muscle wasting diseases, cachexia, Cushing’s syndrome, anti-psychotic drug induced weight gain, obesity, post-traumatic stress disorder and alcoholism. Over two-hundred-seventy compounds I were prepared For example, heating a mixture of 3-(benzo[b]thiophen-3-ylmethylene)pentane-2,4-dione, Me 3-oxobutanoate and 30% aqueous ammonium in iso-PrOH at reflux temperature for 12 h afforded 25% II (both enantiomers were separated). Exemplified compounds I were evaluated for their androgen receptor and glucocorticoid receptor modulatory activities (data given for representative compounds I). The experimental process involved the reaction of 5-Chlorobenzo[b]thiophene-3-carbaldehyde(cas: 16296-68-7).Application In Synthesis of 5-Chlorobenzo[b]thiophene-3-carbaldehyde

The Article related to pyridine dihydropyridine preparation nuclear androgen glucocorticoid receptor modulator antitumor, benign prostate hyperplasia polycystic ovary syndrome treatment dihydropyridine preparation, hair loss hirsutism acne hypogonadism treatment dihydropyridine pyridine preparation and other aspects.Application In Synthesis of 5-Chlorobenzo[b]thiophene-3-carbaldehyde

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem