Heterocyclic Building Blocks-Benzothiophene

Raju, Telugu Bhim’s team published research in RSC Advances in 4 | CAS: 1426829-76-6

RSC Advances published new progress about 1426829-76-6. 1426829-76-6 belongs to benzothiophene, auxiliary class Other Aromatic Heterocyclic,Bromide, name is 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, and the molecular formula is C21H26Br4S2, Safety of 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene.

Raju, Telugu Bhim published the artcileHighly efficient and facile alkylation of 4H-cyclopenta-[2,1-b:3,4-b’]dithiophene in water, Safety of 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, the publication is RSC Advances (2014), 4(71), 37738-37745, database is CAplus.

A new and highly convenient method to perform alkylation of 4H-cyclopenta-[2,1-b:3,4-b’]dithiophene (CPDT) in aqueous conditions is reported. This method was also extended to successfully perform alkylation of 2,6-dibromo-4H-cyclopenta-[2,1-b:3,4-b’]dithiophene for the first time. This facile method has several advantages such as the exclusive use of water instead of high boiling toxic solvents, simple separation of the defect free dialkylated CPDT product I (Y = H, Br; R = hexyl, octyl, 5-bromopentyl, etc.) and the use of mild reaction conditions. Despite using mild reagents and reaction conditions, very high yields of up to 98% pure dialkylated CPDT products I are obtained much more readily by this method in less time than literature procedures. The desired dialkylated product with the alkyl halides used here.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Chapman, Norman Bellamy’s team published research in Journal of the Chemical Society [Section] C: Organic in | CAS: 17515-00-3

Journal of the Chemical Society [Section] C: Organic published new progress about 17515-00-3. 17515-00-3 belongs to benzothiophene, auxiliary class 5.6_Aromatics,Benzothiophens, name is 5-(tert-Butyl)benzo[b]thiophene, and the molecular formula is C12H14S, HPLC of Formula: 17515-00-3.

Chapman, Norman Bellamy published the artcileProton magnetic resonance spectra of some benzo[b]thiophene derivatives, HPLC of Formula: 17515-00-3, the publication is Journal of the Chemical Society [Section] C: Organic (1968), 764-9, database is CAplus.

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.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Lyu, Yan’s team published research in Angewandte Chemie, International Edition in 56 | CAS: 1426829-76-6

Angewandte Chemie, International Edition published new progress about 1426829-76-6. 1426829-76-6 belongs to benzothiophene, auxiliary class Other Aromatic Heterocyclic,Bromide, name is 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, and the molecular formula is C21H26Br4S2, Recommanded Product: 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene.

Lyu, Yan published the artcileDendronized Semiconducting Polymer as Photothermal Nanocarrier for Remote Activation of Gene Expression, Recommanded Product: 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, the publication is Angewandte Chemie, International Edition (2017), 56(31), 9155-9159, database is CAplus and MEDLINE.

Regulation of transgene systems is needed to develop innovative medicines. However, noninvasive remote control of gene expression has been rarely developed and remains challenging. We herein synthesize a near-IR (NIR) absorbing dendronized semiconducting polymer (DSP) and utilize it as a photothermal nanocarrier not only to efficiently deliver genes but also to spatiotemporally control gene expression in conjunction with heat-inducible promoter. DSP has a high photothermal conversion efficiency (44.2 %) at 808 nm, permitting fast transduction of NIR light into thermal signals for intracellular activation of transcription. Such a DSP-mediated remote activation can rapidly and safely result in 25- and 4.5-fold increases in the expression levels of proteins in living cells and mice, resp. This study thus provides a promising approach to optically regulate transgene systems for on-demand therapeutic transgene dosing.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Li, Jingchao’s team published research in Angewandte Chemie, International Edition in 58 | CAS: 1426829-76-6

Li, Jingchao published the artcileOrganic Semiconducting Pro-nanostimulants for Near-Infrared Photoactivatable Cancer Immunotherapy, Formula: C21H26Br4S2, the publication is Angewandte Chemie, International Edition (2019), 58(36), 12680-12687, database is CAplus and MEDLINE.

In this study, an organic semiconducting pro-nanostimulant (OSPS) with a near-IR (NIR) photoactivatable immunotherapeutic action for synergetic cancer therapy is presented. OSPS comprises a semiconducting polymer nanoparticle (SPN) core and an immunostimulant conjugated through a singlet oxygen (¹O₂) cleavable linkers. Upon NIR laser irradiation, OSPS generates both heat and ¹O₂ to exert combinational phototherapy not only to ablate tumors but also to produce tumor-associated antigens. More importantly, NIR irradiation triggers the cleavage of ¹O₂-cleavable linkers, triggering the remote release of the immunostimulants from OSPS to modulate the immunosuppressive tumor microenvironment. Thus, the released tumor-associated antigens in conjunction with activated immunostimulants induce a synergistic antitumor immune response after OSPS-mediated phototherapy, resulting in the inhibited growth of both primary/distant tumors and lung metastasis in a mouse xenograft model, which is not observed for sole phototherapy.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Jiang, Yuyan’s team published research in Biomaterials in 145 | CAS: 1426829-76-6

Biomaterials published new progress about 1426829-76-6. 1426829-76-6 belongs to benzothiophene, auxiliary class Other Aromatic Heterocyclic,Bromide, name is 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, and the molecular formula is C21H26Br4S2, Name: 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene.

Jiang, Yuyan published the artcileAmphiphilic semiconducting polymer as multifunctional nanocarrier for fluorescence/photoacoustic imaging guided chemo-photothermal therapy, Name: 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, the publication is Biomaterials (2017), 168-177, database is CAplus and MEDLINE.

Chemo-photothermal nanotheranostics has the advantage of synergistic therapeutic effect, providing opportunities for optimized cancer therapy. However, current chemo-photothermal nanotheranostic systems generally comprise more than three components, encountering the potential issues of unstable nanostructures and unexpected conflicts in optical and biophys. properties among different components. We herein synthesize an amphiphilic semiconducting polymer (PEG-PCB) and utilize it as a multifunctional nanocarrier to simplify chemo-photothermal nanotheranostics. PEG-PCB has a semiconducting backbone that not only serves as the diagnostic component for near-IR (NIR) fluorescence and photoacoustic (PA) imaging, but also acts as the therapeutic agent for photothermal therapy. In addition, the hydrophobic backbone of PEG-PCB provides strong hydrophobic and π-π interactions with the aromatic anticancer drug such as doxorubicin for drug encapsulation and delivery. Such a trifunctionality of PEG-PCB eventually results in a greatly simplified nanotheranostic system with only two components but multimodal imaging and therapeutic capacities, permitting effective NIR fluorescence/PA imaging guided chemo-photothermal therapy of cancer in living mice. Our study thus provides a mol. engineering approach to integrate essential properties into one polymer for multimodal nanotheranostics.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Chapman, Norman Bellamy’s team published research in Journal of the Chemical Society [Section] C: Organic in 5 | CAS: 17515-00-3

Chapman, Norman Bellamy published the artcilePharmacologically active benzo[b]thiophene derivatives. IV. 5- and 6-Alkyl derivatives with an N-alkyl-N-(2-chloroethyl)aminomethyl group in the 3-position, Product Details of C12H14S, the publication is Journal of the Chemical Society [Section] C: Organic (1968), 514-17, database is CAplus and MEDLINE.

3-Chloromethylbenzo[b]thiophene reacted with N-ethyl-, N-isopropyl-, N-butyl-, N-tert-butyl, or N-benzylethanolamine to give the corresponding N-alkyl – N – (2 – hydroxyethyl) – 3 – aminomethylbenzo[b]thiophene derivatives With SOCl2 in dry CHCl3 these amino alcs. gave the corresponding N-alkyl-N-(2-chloroethyl)-3-aminomethylbenzo[b]thiophene hydrochlorides. A similar range of compounds was obtained from 5- or 6-methylbenzo[b]thiophene but only the N-Et derivative was prepared from 5-ethyl-, 5-isopropyl-, or 5-tert – butylbenzo[b]thiophene. N,N – Bis(2 – hydroxyethyl) – 3-aminomethylbenzo[b]thiophene and its 5-Et derivative were also prepared and converted into the corresponding nitrogen mustards. These compounds were evaluated pharmacol., with special emphasis on their anti-5HT and antitumor activity.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Rosendorff, C’s team published research in South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde in 1980-06-28 | CAS: 40180-04-9

South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde published new progress in MEDLINE about 40180-04-9, 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Recommanded Product: 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid.

Rosendorff, C published the artcileThe treatment of mild to moderate essential hypertension with tienilic acid (ticrynafen)., Recommanded Product: 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, the main research area is .

This paper reports a clinical trial of tienilic acid, a new diuretic with uricosuric properties, in 23 patients with mild to moderate hypertension (standing diastolic blood pressure 90-120 mmHg). Tienilic acid was compared with hydrochlorothiazide in a variable-dose, double-blind cross-over study, and the duration of therapy was 8 weeks for each drug. The falls in blood pressure (systolic/diastolic) were: 11/11 mmHg supine and 17/11 mmHg standing for tienilic acid, and 8/12 mmHg supine and 9/17 mmHg standing for hydrochlorothiazide. There were no significant differences between the two drugs in their effect on blood pressure and heart rate, and regarding side-effects and laboratory results, except for serum uric levels (mean fall of 1,5 mg/dl with tienilic acid and mean increase of 1.1 mg/l with ydrochlorothiazide).

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Ambrosioni, E’s team published research in International journal of clinical pharmacology, therapy, and toxicology in 1981 | CAS: 40180-04-9

International journal of clinical pharmacology, therapy, and toxicology published new progress in MEDLINE about 40180-04-9, 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Quality Control of 40180-04-9.

Ambrosioni, E published the artcileEffects of tienilic acid used alone and in association with triamterene or amiloride on urinary excretion of electrolytes., Quality Control of 40180-04-9, the main research area is .

The K-sparing effects of amiloride (A) and triamterene (T) associated with tienilic acid (C) are studied, along with their effects on diuresis and on the urinary excretion of uric acid, Mg, Na, Cl, P, and Ca. Eighteen hospitalized patients, divided into two groups of nine, received the following dosages of the drugs. The first group took 250 mg of C (equivalent to 50 mg hydrochlorothiazide), 5 mg of A and 100 mg of T; the second received double doses of both A and T but the same dose of C. Each treatment was administered on 2 not necessarily consecutive days, so as to have a total of 6 days of treatment per patient according to a balanced randomized design identical for the two groups. The data were obtained from urine collected during the first 8 h after the drug was administered, and during the following 16 h. A and T showed a significant K-sparing effect (p less than 0.01) only for the second group, and only at the higher dosages were minor effects on the urinary excretion of uric acid, Mg, and Cl noted (p less than 0.05). The association of A or T with C was well tolerated, and no important side effects were observed.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Prandota, J’s team published research in International journal of clinical pharmacology, therapy, and toxicology in 1980 | CAS: 40180-04-9

Prandota, J published the artcileEffect of tienilic acid (Diflurex) on the binding of warfarin 14C to human plasma proteins., Product Details of C13H8Cl2O4S, the main research area is .

Tienilic acid (Diflurex), a new diuretic with a chemical structure close to that of ethacrynic acid, displaces significant amounts of warfarin from 2 g/l human albumin in vitro by a competitive mechanism. When physiologic concentrations of human albumin are used, or with human plasma there is no such interaction. Because excessive hypoprothrombinaemia and haemorrhage were reported in vivo when tienilic acid was added to oral coumarin anticoagulant therapy, it is advised to use another diuretic if necessary.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Maass, A R’s team published research in Clinical and experimental hypertension. Part A, Theory and practice in 1982 | CAS: 40180-04-9

Clinical and experimental hypertension. Part A, Theory and practice published new progress in MEDLINE about 40180-04-9, 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, SDS of cas: 40180-04-9.

Maass, A R published the artcilePharmacokinetics and mode of action of tienilic acid., SDS of cas: 40180-04-9, the main research area is .

A review of the absorption, distribution, metabolism and excretion of ticrynafen (tienilic acid) in 8 animal species, including man, is presented. Although some species effects are apparent, ticrynafen absorption is essentially complete following oral administration. The compound is extensively bound to plasma proteins, primarily albumin. Consequently, tissue concentrations are generally lower than plasma concentrations. Plasma and whole body clearance of ticrynafen is rapid due both to metabolism and to extensive renal excretion of the compound and its metabolites. Male/female differences in renal excretion occur, with a subsequent effect on ticrynafen metabolism. Ticrynafen is an inhibitor of reabsorption of sodium and uric acid by the kidney. This inhibitory effect, within the renal tubular lumen, accounts for its diuretic and uricosuric activity and could account for its antihypertensive activity, although a direct effect has also been claimed. Ticrynafen is also a classical example of a competitive inhibitor of organic acid transport in the kidney and other organs. Much of the drug-drug interaction involving ticrynafen is understandable due to its effect on transport. However, potentiation of anticoagulant activity appears to involve some direct effects upon warfarin metabolism although ticrynafen, in general, is not an enzyme inducer or inhibitor. Toxicity of ticrynafen is low in all animal species.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem