Category: 147181-08-6

Van Zandt, Michael C. published the artcileDesign and synthesis of highly potent and selective (2-arylcarbamoyl-phenoxy)-acetic acid inhibitors of aldose reductase for treatment of chronic diabetic complications, SDS of cas: 147181-08-6, the publication is Bioorganic & Medicinal Chemistry (2004), 12(21), 5661-5675, database is CAplus and MEDLINE.

Recent efforts to identify treatments for chronic diabetic complications have resulted in the discovery of a novel series of highly potent and selective (2-arylcarbamoyl-phenoxy)-acetic acid aldose reductase inhibitors. The compound class features a core template that utilizes an intramol. hydrogen bond to position the key structural elements of the pharmacophore in a conformation, which promotes a high binding affinity. The lead candidate, I, 5-fluoro-2-(4-bromo-2-fluoro-benzylthiocarbamoyl)-phenoxyacetic acid, inhibits aldose reductase with an IC₅₀ of 30 nM, while being 1100 times less active against aldehyde reductase, a related enzyme involved in the detoxification of reactive aldehydes. In addition, I lowers nerve sorbitol levels with an ED₅₀ of 31 mg/kg/d po in the 4-day STZ-induced diabetic rat model.

Bioorganic & Medicinal Chemistry published new progress about 147181-08-6. 147181-08-6 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Salt,Amine,Benzene, name is (4-Bromo-2-fluorophenyl)methanamine hydrochloride, and the molecular formula is C4H6O3, SDS of cas: 147181-08-6.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Malamas, Michael S. published the artcileFacile synthesis of novel spiro[azetidine-2,4′(1’H)-isoquinoline-1′,3′,4(2’H)-triones], Application of (4-Bromo-2-fluorophenyl)methanamine hydrochloride, the publication is Journal of Heterocyclic Chemistry (1994), 31(2), 565-8, database is CAplus.

A convenient general method for the synthesis of a new heterocycle, spiro[azetidine-2,4′(1’H)-isoquinoline-1′,3′,4(2’H)-trione] (I, R¹ = H, halo; R² = Me, CH₂C₆H₃FBr-2,4) is described. The key intermediate II (R = Cl) was prepared by direct halogenation of position-4 of acid II (R = H) with thionyl chloride, and subsequent treatment of the generated 4-Cl, 4-acetyl chloride derivative with a THF/NH₃ solution at low temperature

Journal of Heterocyclic Chemistry published new progress about 147181-08-6. 147181-08-6 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Salt,Amine,Benzene, name is (4-Bromo-2-fluorophenyl)methanamine hydrochloride, and the molecular formula is C7H8BrClFN, Application of (4-Bromo-2-fluorophenyl)methanamine hydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Lenstra, Danny C. published the artcileCatalytic Staudinger Reduction at Room Temperature, Application of (4-Bromo-2-fluorophenyl)methanamine hydrochloride, the publication is Journal of Organic Chemistry (2019), 84(10), 6536-6545, database is CAplus and MEDLINE.

We report an efficient catalytic Staudinger reduction at room temperature that enables the preparation of a structurally diverse set of amines from azides in excellent yields. The reaction is based on the use of catalytic amounts of triphenylphosphine as a phosphine source and diphenyldisiloxane as a reducing agent. Our catalytic Staudinger reduction exhibits a high chemoselectivity, as exemplified by reduction of azides over other common functionalities, including nitriles, alkenes, alkynes, esters, and ketones.

Journal of Organic Chemistry published new progress about 147181-08-6. 147181-08-6 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Salt,Amine,Benzene, name is (4-Bromo-2-fluorophenyl)methanamine hydrochloride, and the molecular formula is C7H8BrClFN, Application of (4-Bromo-2-fluorophenyl)methanamine hydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Li, Xin published the artcileInfluence of polybenzimidazole main chain structure on H₂/CO₂ separation at elevated temperatures, COA of Formula: C7H8BrClFN, the publication is Journal of Membrane Science (2014), 59-68, database is CAplus.

Four polybenzimidazole (PBI) derivatives were prepared to study the effects of main chain chem. and structure on H₂/CO₂ perm-selectivity of cast films. These structural variations were designed to exhibit high localized mobility at elevated temperatures, contain rigid and bent configurations that frustrated close chain packing, or possess bulky side groups. The modified PBIs exhibited high mol. weights, slightly lower thermal stabilities, and higher organo-solubilities compared with com. m-PBI. Dilute polymer solutions (<3.0 wt%) were used to fabricate high quality thin films under carefully optimized film processing conditions. Gas permeation properties of these PBI films were evaluated at elevated temperatures (up to 250 °C) and pressures (up to 50 psia). The main chain structural variations effectively disrupted the PBI chain packing resulting in much improved film H₂ permeability (up to 997.2 barrer) compared with m-PBI (76.81 barrer) at 250 °C and 50 psia. However, lower H₂/CO₂ selectivities (5-7 (modified PBIs) vs. 23 (m-PBI)) were also measured and reflected the general trade-off between gas permeability and selectivity. When tested at 250 °C, PBI-based materials exhibited gas separation performance higher than the Robeson upper bound prediction and are promising materials for high temperature H₂ separation from syngas.

Journal of Membrane Science published new progress about 147181-08-6. 147181-08-6 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Salt,Amine,Benzene, name is (4-Bromo-2-fluorophenyl)methanamine hydrochloride, and the molecular formula is C7H8BrClFN, COA of Formula: C7H8BrClFN.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Negoro, Toshiyuki published the artcileNovel, Highly Potent Aldose Reductase Inhibitors: (R)-(-)-2-(4-Bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine- 4-spiro-3′-pyrrolidine-1,2′,3,5′-tetrone (AS-3201) and Its Congeners, COA of Formula: C7H8BrClFN, the publication is Journal of Medicinal Chemistry (1998), 41(21), 4118-4129, database is CAplus and MEDLINE.

A series of novel tetrahydropyrrolo[1,2-a]pyrazine derivatives were synthesized and evaluated as aldose reductase inhibitors on the basis of their abilities to inhibit porcine lens aldose reductase in vitro and to inhibit sorbitol accumulation in the sciatic nerve of streptozotocin-induced diabetic rats in vivo. Of these compounds, spirosuccinimide-fused tetrahydropyrrolo[1,2-a]pyrazine-1,3-dione derivatives showed significantly potent aldose reductase inhibitory activity. In the in vivo activity of these derivatives, 2-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-spiro-3′-pyrrolidine-1,2′,3,5′-tetrone (I) (SX-3030) showed the best oral activity. The enantiomers of I were synthesized, and the biol. activities were evaluated. It was found that aldose reductase inhibitory activity resides in the (-)-I (AS-3201), which was 10 times more potent in inhibition of the aldose reductase (IC₅₀ = 1.5 × 10^-8 M) and 500 times more potent in the in vivo activity (ED₅₀ = 0.18 mg/kg/day for 5 days) than the corresponding (+)-I (SX-3202). From these results, AS-3201 was selected as the candidate for clin. development. The absolute configuration of AS-3201 was also established to be (R)-form by single-crystal X-ray anal. In this article we report the preparation and structure-activity relationship of tetrahydropyrrolopyrazine derivatives including a novel aldose reductase inhibitor, AS-3201.

Journal of Medicinal Chemistry published new progress about 147181-08-6. 147181-08-6 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Salt,Amine,Benzene, name is (4-Bromo-2-fluorophenyl)methanamine hydrochloride, and the molecular formula is C7H8BrClFN, COA of Formula: C7H8BrClFN.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Malamas, Michael S. published the artcileNovel Spirosuccinimide Aldose Reductase Inhibitors Derived from Isoquinoline-1,3-diones: 2-[(4-Bromo-2-fluorophenyl)methyl]-6-fluorospiro[isoquinoline-4(11H),3′-pyrrolidine]-1,2′,3,5′(2H)-tetrone and Congeners. 1, Computed Properties of 147181-08-6, the publication is Journal of Medicinal Chemistry (1994), 37(13), 2043-58, database is CAplus and MEDLINE.

Spiro[isoquinolinepyrrolidine]tetrones I [R¹ = H, Cl, F, Br, OMe, CF₃, Me, NO₂; R² = (un)substituted benzyl, benzothiazolylmethyl, alkyl] were prepared and evaluated in vitro for their ability to inhibit glyceraldehyde reduction, using a partially purified bovine lens aldose reductase preparation, and in vivo for their ability to inhibit galactitol accumulation in the lens and sciatic nerve of galactose-fed rats. Substitution at the N-2 position of I with diverse structural substituents (i.e., aralkyl, benzothiazolylmethyl, methyl) produced several excellent series of aldose reductase inhibitors. Optimization of these new series of spirosuccinimides through structure-activity relationship (SAR) studies, including analogy from other drug series (ponalrestat, zopolrestat), led to the design of the clin. candidate I [R¹ = 6-F, R² = 2,4-F(Br)C₆H₃, II]. II exhibited exceptional oral potency in two animal models of diabetic complications, the 14-day galactose-fed and streptozocin-induced diabetic rats, with ED₅₀ values for the sciatic nerve of 0.1 and 0.09 mg/kg/day, resp. Both enantiomeric forms of II exhibited similar inhibitory activity in both in vitro and in vivo assays possibly due to their rapid interconversion. In an ex vivo experiment, the pharmacodynamic effect of II in the plasma of rats and dogs, after a single dose, appeared to be comparable to that of tolrestat.

Journal of Medicinal Chemistry published new progress about 147181-08-6. 147181-08-6 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Salt,Amine,Benzene, name is (4-Bromo-2-fluorophenyl)methanamine hydrochloride, and the molecular formula is C7H8BrClFN, Computed Properties of 147181-08-6.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Lenstra, Danny C. published the artcileSustainable organophosphorus-catalysed Staudinger reduction, SDS of cas: 147181-08-6, the publication is Green Chemistry (2018), 20(19), 4418-4422, database is CAplus.

A highly efficient and sustainable catalytic Staudinger reduction for the conversion of organic azides to amines in excellent yields was developed. The reaction displayed excellent functional group tolerance to functionalities that were otherwise prone to reduction, such as sulfones, esters, amides, ketones, nitriles, alkenes and benzyl ethers. The green nature of the reaction was exemplified by the use of PMHS, CPME and a lack of column chromatog.

Green Chemistry published new progress about 147181-08-6. 147181-08-6 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Salt,Amine,Benzene, name is (4-Bromo-2-fluorophenyl)methanamine hydrochloride, and the molecular formula is C7H8BrClFN, SDS of cas: 147181-08-6.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary