Tag: M.W=250-300

Chang, Linda L. published the artcilePotent and orally active angiotensin II receptor antagonists with equal affinity for human AT₁ and AT₂ subtypes, Application In Synthesis of 76283-09-5, the publication is Journal of Medicinal Chemistry (1995), 38(19), 3741-58, database is CAplus and MEDLINE.

In order to block the effects induced by the interactions between angiotensin II (AII) and both AT₁ and AT₂ receptors, the authors have pursued the discovery of orally active non-peptide AII antagonists that exhibit potent and equal affinity for human AT₁ and AT₂ receptor subtypes. A series of previously prepared nanomolar (IC₅₀) trisubstituted 1,2,4-triazolinone biphenylsulfonamide dual-acting AII antagonists has been modified at five different positions in order to increase AT₂ binding affinity, maintain AT₁ activity, and reduce the human adrenal AT₂/AT₁ potency ratio (IC₅₀ ratio) from ≥10. The targeted human adrenal potency ratio of ≤1 was achieved with a number of compounds possessing an Et group at C⁵ of the triazolinone and a 3-fluoro substituent at the N⁴-biarylmethyl moiety. The most favored of these was triazolinone I which exhibited subnanomolar potency at both the AT₁ (rabbit aorta) and AT₂ (rat midbrain) receptors, with a slight preference for the latter, and had a human adrenal AT₂/AT₁ IC₅₀ ratio of 1. This tert-Bu sulfonylcarbamate had excellent i.v. activity at 1 mg/kg (100% peak inhibition, ≥4 h duration of action) and is orally active at 3 mg/kg with >6 h duration of action in a conscious rat model. The present study shows that the NH of the amide on the N²-aryl moiety is not required for subnanomolar binding affinity to either receptor subtype, although a keto functionality at this position is essential for acceptable AT₂ binding. Receptor-ligand binding interactions derived from the structure-activity relationships are discussed with respect to both receptor subtypes.

Journal of Medicinal Chemistry published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Application In Synthesis of 76283-09-5.

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

Wang, Kai published the artcileSolvent Annealing Effects in Dithieno[3,2-b:2′,3′-d]pyrrole-5,6-Difluorobenzo[c][1,2,5]thiadiazole Small Molecule Donors for Bulk-Heterojunction Solar Cells, Recommanded Product: 2-Bromo-3-(2-ethylhexyl)thiophene, the publication is Chemistry of Materials (2016), 28(15), 5415-5425, database is CAplus.

Low-bandgap small mol. (SM) donors that can be solution-processed with fullerene acceptors (e.g., PC₆₁/₇₁BM) are proving to be particularly promising in bulk-heterojunction (BHJ) solar cells. Compared to their π-conjugated polymer counterparts, SM donors are well-defined (monodisperse) and more synthetically modular, with relatively wide ranges of bandgaps that can be achieved in stepwise couplings of various donor and acceptor motifs. However, the optimization of SM-fullerene morphologies and BHJ device efficiencies relies more specifically on the use of processing additives, postprocessing thermal, or solvent vapor annealing (SVA) approaches, and achieving adequate interpenetrating networks and structural order in BHJ thin films can be challenging. In this report, we examine the correlated effects of mol. structure and postprocessing SVA on the BHJ solar cell performance of a set of π-extended SM donors composed of dithieno[3,2-b:2′,3′-d]pyrrole (DTP) and 5,6-difluorobenzo[c][1,2,5]thiadiazole ([2F]BT) units. In these systems (SM1-SM3), the introduction of addnl. alkyl substituents and unsubstituted thiophene rings on the peripheral unit groups critically impacts the effects of SVA steps on BHJ solar cell efficiency. We show that the more π-extended and alkyl-substituted analog SM3 stands out, with BHJ device efficiencies of ∼6% obtained from SVA with CS₂, while SVA-treated SM3-based active layers also show the most favorable ordering and carrier mobility patterns. However, unlike numbers of SM donors reported in recent years, DTP-[2F]BT SM analogs are in general not prone to dramatic performance variations in BHJ thin films cast with processing additives. Our results indicate that the role of SVA steps is not independent of the mol. structure of the SM donors used in the BHJ solar cells.

Chemistry of Materials published new progress about 303734-52-3. 303734-52-3 belongs to bromides-buliding-blocks, auxiliary class Thiophene,Bromide, name is 2-Bromo-3-(2-ethylhexyl)thiophene, and the molecular formula is C3H5F3O, Recommanded Product: 2-Bromo-3-(2-ethylhexyl)thiophene.

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

Chen, Fengli published the artcileA comparative study of C₂H₂ adsorption properties in five isomeric copper-based MOFs based on naphthalene-derived diisophthalates, Recommanded Product: 1,3-Dibromonaphthalene, the publication is Dalton Transactions (2017), 46(34), 11469-11478, database is CAplus and MEDLINE.

Five positional isomeric ligands consisting of two peripheral isophthalate moieties attached to the central naphthyl core in different ways, namely, 5,5′-(naphthyl-1,3-diyl)diisophthalate (H₄L1), 5,5′-(naphthyl-1,4-diyl)diisophthalate (H₄L2), 5,5′-(naphthyl-1,5-diyl)diisophthalate (H₄L3), 5,5′-(naphthyl-1,6-diyl)diisophthalate (H₄L4) and 5,5′-(naphthyl-2,6-diyl)diisophthalate (H₄L5), were used to generate five Cu-based MOF isomers. As revealed by single-crystal x-ray diffraction studies, they adopted two different types of topologies depending on the organic ligands: ssa topol. for the MOFs ZJNU-71 and ZJNU-74 based on the ligands H₄L1 and H₄L4, resp., and nbo topol. for the MOFs ZJNU-72, ZJNU-73 and NOTT-103 derived from the ligands H₄L2, H₄L3 and H₄L5, resp. Also, their C₂H₂ adsorption properties were systematically studied, revealing that their different C₂H₂ uptake capacities can be mainly related to their different pore sizes since they possess the same chem. compositions and gravimetric densities of open metal sites. In particular, among these five MOF compounds studied, ZJNU-71 exhibits the highest gravimetric C₂H₂ uptake of 208.1 cm³ (STP) g^-1 at 295 K and 1 atm. The value is also among the highest reported for MOF compounds under the same conditions. This work provides a fundamental understanding of the impact of the positional isomerism of the organic ligands on the structures as well as gas adsorption properties of the resulting MOFs.

Dalton Transactions published new progress about 52358-73-3. 52358-73-3 belongs to bromides-buliding-blocks, auxiliary class Bromide,Naphthalene, name is 1,3-Dibromonaphthalene, and the molecular formula is C10H6Br2, Recommanded Product: 1,3-Dibromonaphthalene.

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

Gao, Feng published the artcileDipolar HCP materials as alternatives to DMF solvent for azide-based synthesis, Application of 4-Bromo-1-(bromomethyl)-2-fluorobenzene, the publication is Green Chemistry (2021), 23(19), 7499-7505, database is CAplus.

Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO₃H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN₃ to benzylic azides and 1,2,3-triazoles in EtOH (95%), resp., avoiding the use of risky DMF and improving the separation processes of the products.

Green Chemistry published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Application of 4-Bromo-1-(bromomethyl)-2-fluorobenzene.

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

Wei, Changyong published the artcileDevelopment of GLUT4-selective antagonists for multiple myeloma therapy, Application In Synthesis of 1997-80-4, the publication is European Journal of Medicinal Chemistry (2017), 573-586, database is CAplus and MEDLINE.

Cancer cells consume more glucose to fuel metabolic programs fundamental to sustaining their survival, growth and proliferation. Among the fourteen SLC2A family members, GLUTs 1 and 4 are high-affinity glucose transporters. GLUT4 (SLC2A4) is highly expressed in muscle and adipose tissue. Basally retained within the cell, GLUT4 traffics to the plasma membrane (PM) in response to insulin and exercise-stimulation. The plasma cell malignancy multiple myeloma (MM) exhibits increased constitutive expression of GLUT4 on the PM, co-opting use of GLUT4 for survival and proliferation. GLUT4 inhibition by knockdown or treatment with the FDA-approved HIV protease inhibitor ritonavir leads to cytostatic and/or cytotoxic and chemosensitizing effects in tumor cells both in vitro and in vivo. We recently reported our generation of GLUT4 homol. models and virtual high-throughput screening (vHTS) to identify multiple series of novel GLUT4 antagonists. In this report, we describe our initial hit-to-lead optimization to synthesize new analogs with improved potency and selectivity for GLUT4, and the biol. characterization of these compounds in a variety of assays. We show that our lead compound (compound 20) decreases glucose uptake and cell proliferation as well as inhibits the expression of pro-survival MCL-1 in MM similar to the effect observed via knockdown of GLUT4 expression. Compound 20 is also effective at chemosensitizing multiple myeloma cell lines and patient samples to venetoclax, dexamethasone and melphalan. In sum, we report development of selective GLUT4 inhibitors lacking inhibitory activity against GLUT1 and GLUT8. We show that selective pharmacol. inhibition of GLUT4 is feasible and this may represent a novel strategy for the treatment and chemosensitization of multiple myeloma to standard therapeutics.

European Journal of Medicinal Chemistry published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C13H10O2, Application In Synthesis of 1997-80-4.

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

Picard, Franck published the artcileSynthesis and Evaluation of 2′-Substituted 4-(4′-Carboxy- or 4′-carboxymethylbenzylidene)-N-acylpiperidines: Highly Potent and in Vivo Active Steroid 5α-Reductase Type 2 Inhibitors, Formula: C7H5Br2F, the publication is Journal of Medicinal Chemistry (2002), 45(16), 3406-3417, database is CAplus and MEDLINE.

Sixteen N-acylpiperidines I (R¹ = Ph₂CH, Ph₂CHCH₂, dicyclohexylmethyl, 1-adamantyl; R² = H, F, MeO; R³ = H, HO₂C; R⁴ = H, HO₂C, HO₂CCH₂) and II (R⁵ = Ph₂CH, Ph₂N, Me₃CO, 1-adamantyl), bearing carboxylic acid moieties, were synthesized and evaluated for inhibition of rat and human steroid 5α-reductase isoenzymes types 1 and 2. In the dicyclohexylacetyl series (R¹ = dicyclohexylmethyl), fluorination in the 2-position of the benzene nucleus, exchange of the carboxy group by a carboxymethyl moiety, and combination of both structural modifications led to highly active inhibitors of the human type 2 isoenzyme [IC₅₀ values: I [R² = F, R³ = H, R⁴ = HO₂C; (III)], 11 nM; I (R² = R³ = H, R⁴ = HO₂CCH₂), 6 nM; I (R² = F, R³ = H, R⁴ = HO₂CCH₂), 7 nM; finasteride, 5 nM]. In vivo all compounds tested markedly reduced the prostate weights in castrated testosterone-treated rats. Oral activity was shown for compound I (R¹ = dicyclohexylmethyl, R² = R³ = H, R⁴ = HO₂C). From the finding that III is active in the rat, although it is a rather poor inhibitor of the rat enzyme and is a strong inhibitor of the human enzyme, it is concluded that it should be highly potent in men.

Journal of Medicinal Chemistry published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Formula: C7H5Br2F.

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

Goeker, Hakan published the artcileSynthesis and potent antifungal activity against Candida species of some novel 1H-benzimidazoles, Safety of 4-Bromo-N-butyl-2-nitroaniline, the publication is Journal of Heterocyclic Chemistry (2009), 46(5), 936-948, database is CAplus.

A series of 47 novel N¹-alkylated-2-aryl-5(6)-substituted-1H-benzimidazoles and their three novel indole analogs were synthesized and evaluated for in vitro antifungal activities against Candida species by the tube dilution method. The results showed that I and II, having pyridine at the position C-2, of benzimidazoles exhibited the greatest activity with MIC values of 6.25-3.12 μg/mL. Indole analogs III (R¹ = H, R² = Br; R¹ = Pr, R² = Br, CN) have no inhibitory activity.

Journal of Heterocyclic Chemistry published new progress about 1036461-93-4. 1036461-93-4 belongs to bromides-buliding-blocks, auxiliary class Benzenes, name is 4-Bromo-N-butyl-2-nitroaniline, and the molecular formula is C10H13BrN2O2, Safety of 4-Bromo-N-butyl-2-nitroaniline.

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

Yagui, Javier published the artcileBenzodithiophene-based small molecules for vacuum-processed organic photovoltaic devices, Recommanded Product: 2-Bromo-3-(2-ethylhexyl)thiophene, the publication is Optical Materials (Amsterdam, Netherlands) (2020), 110354, database is CAplus.

Benzo[1,2-b:4,5-b’]dithiophene (BDT) derivatives were evaluated as donor materials for the first time in vacuum-processed organic photovoltaic (OPV) devices. Simple BDT derivatives coupled with thiophene, 3-methylthiophene, and 3-(2-ethylhexyl)thiophene, I [R = H, Me, CH₂CH(Et)(CH₂)₃Me], were synthesized and characterized as part of this evaluation study. Similar frontier MOs were determined for the three mols. by DFT calculations, optical, and electrochem. measurements. Therefore, the effect of the alkyl substituents on the film morphol. and mol. order was possible to evaluate as well. All mols. exhibited thermal stability for their co-evaporation with C60 to form bulk heterojunction layers in OPV devices. An increase in short-circuit c.d. was observed for devices with compound I [R = Me]. Microscopy images and hole-transport measurements suggested an induced mol. order by the Me group of compound I [R = Me] on the active layer. Although low photoconversion efficiency values were obtained (∼1.2%), this work demonstrates the feasibility to fabricate fully vacuum-processed OPV devices with BDT derivatives as donor materials. Devices with higher photoconversion efficiencies were expected for BDT derivatives with enhanced optoelectronic properties.

Optical Materials (Amsterdam, Netherlands) published new progress about 303734-52-3. 303734-52-3 belongs to bromides-buliding-blocks, auxiliary class Thiophene,Bromide, name is 2-Bromo-3-(2-ethylhexyl)thiophene, and the molecular formula is C24H20Ge, Recommanded Product: 2-Bromo-3-(2-ethylhexyl)thiophene.

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

Mylari, Banavara L. published the artcileA novel series of non-carboxylic acid, non-hydantoin inhibitors of aldose reductase with potent oral activity in diabetic rat models: 6-(5-chloro-3-methylbenzofuran-2-sulfonyl)-2H-pyridazin-3-one and congeners, Category: bromides-buliding-blocks, the publication is Journal of Medicinal Chemistry (2005), 48(20), 6326-6339, database is CAplus and MEDLINE.

Discovery of a highly selective, potent, and safe non-carboxylic acid, non-hydantoin inhibitor of aldose reductase (AR) capable of potently blocking the excess glucose flux through the polyol pathway that prevails under diabetic conditions has been a long-standing challenge. In response, we did high-throughput screening of our internal libraries of compounds and identified 6-phenylsulfonylpyridazin-2H-3-one, 8, which showed modest inhibition of AR, both in vitro and in vivo. Initial structure-activity relationships concentrated on Ph substituents and led to 6-(2,4-dichlorophenylsulfonyl)-2H-pyridazin-3-one, 8l, which was more potent than 8, both in vitro and in vivo. Incorporation of extant literature findings with other aldose reductase inhibitors, including zopolrestat, resulted in the title inhibitor, 19m, which is one of the most potent and highly selective non-carboxylic acid, non-hydantoin inhibitors of AR yet described (IC₅₀, 1 nM; ED₉₀ vs sciatic nerve sorbitol and fructose, resp., 0.8 and 4.0 mg/kg). In rats, its oral bioavailability is 98% and it has a favorable plasma t_1/2 (26 ± 3 h).

Journal of Medicinal Chemistry published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Category: bromides-buliding-blocks.

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

Dankwardt, Sharon M. published the artcileAmino acid derived sulfonamide hydroxamates as inhibitors of procollagen C-Proteinase. Part 2: Solid-Phase optimization of side chains, Name: 4-Bromo-1-(bromomethyl)-2-fluorobenzene, the publication is Bioorganic & Medicinal Chemistry Letters (2002), 12(8), 1233-1235, database is CAplus and MEDLINE.

Optimization of the amino acid side chain and the N-alkyl group of the sulfonamide of amino acid derived sulfonamide hydroxamates is discussed. The solid-phase synthesis of these potent inhibitors (e.g., I) of procollagen C-proteinase (PCP) is presented. In addition, novel carboxylic acid sulfonamides were discovered to be PCP inhibitors.

Bioorganic & Medicinal Chemistry Letters published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Name: 4-Bromo-1-(bromomethyl)-2-fluorobenzene.

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