Tag: M.W=250-300

Dhungana, Roshan K. published the artcileNi-Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX₂, Category: bromides-buliding-blocks, the publication is Angewandte Chemie, International Edition (2021), 60(42), 22977-22982, database is CAplus and MEDLINE.

We report a Ni-catalyzed regioselective arylbenzylation of alkenylarenes with benzyl halides and arylzinc reagents. The reaction furnishes differently substituted 1,1,3-triarylpropyl structures that are reminiscent of the cores of oligoresveratrol natural products. The reaction is also compatible for the coupling of internal alkenes, secondary benzyl halides and variously substituted arylzinc reagents. Kinetic studies reveal that the reaction proceeds with a rate-limiting single-electron-transfer process and is autocatalyzed by in-situ-generated ZnX₂. The reaction rate is amplified by a factor of three through autocatalysis upon addition of ZnX₂.

Angewandte Chemie, International Edition published new progress about 166821-88-1. 166821-88-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester, name is 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C12H16BBrO2, Category: bromides-buliding-blocks.

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

Iyer, Malliga R. published the artcileProbes for narcotic receptor mediated phenomena. 47.¹ Novel C4a- and N-substituted-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ols, Safety of 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, the publication is Bioorganic & Medicinal Chemistry (2013), 21(11), 3298-3309, database is CAplus and MEDLINE.

A series of N-Me rac-cis-4a-aralkyl- and alkyl-substituted-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ols have been prepared using a simple previously designed synthetic route, to find a ligand that would interact with both μ- and δ-opioid receptors. A C4a-phenethyl derivative I, was found to have modest receptor affinity both at μ- (K_i = 60 nM) and δ-opioid receptors (K_i = 64 nM). The N-Me substituent of I and that of other ligands in the series was then modified to obtain compounds with different N-substituents that might provide higher affinity at both receptors. A number of compounds differently substituted at C4a and N were synthesized and evaluated. Binding studies and functional assays revealed a moderately selective δ-antagonist, selective μ-δ antagonists, and a μ-κ antagonist.

Bioorganic & 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 C9H8BrF3, Safety of 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene.

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

Iyer, Malliga R. published the artcileProbes for narcotic receptor mediated phenomena. N-substituted rac-cis-4a-arylalkyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ols, Synthetic Route of 1997-80-4, the publication is European Journal of Medicinal Chemistry (2015), 531-539, database is CAplus and MEDLINE.

Racemic N-substituted -1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ols containing cis-4a-aralkyl groups were explored as probes for opioid receptors. Specifically cis-4a-phenylpropyl, -phenylbutyl, and-phenylpentyl groups coupled with widely varied substituents on the nitrogen atom were synthesized and their pharmacol. profiles at opioid receptors examined The study yielded compounds with good affinity and moderate to potent antagonist activity at the μ- and δ-opioid receptors, and agonist activity at the κ-opioid receptor. An N-allyl substituent in the C4a phenylpropyl series induced 6-fold higher affinity at δ-than μ-receptors, while an N-CPM substituent in the C4a (CH₂)₃Ph series led to a compound with high δ-affinity and potent δ-antagonist activity.

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 C9H8BrF3, Synthetic Route of 1997-80-4.

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

Schenck Eidam, Hilary published the artcileDiscovery of a First-in-Class Gut-Restricted RET Kinase Inhibitor as a Clinical Candidate for the Treatment of IBS, HPLC of Formula: 76283-09-5, the publication is ACS Medicinal Chemistry Letters (2018), 9(7), 623-628, database is CAplus and MEDLINE.

Abdominal pain and abnormal bowel habits represent major symptoms for irritable bowel syndrome (IBS) patients that are not adequately managed. Although the etiol. of IBS is not completely understood, many of the functions of the gastrointestinal (GI) tract are regulated by the enteric nervous system (ENS). Inflammation or stress-induced expression of growth factors or cytokines may lead to hyperinnervation of visceral afferent neurons in GI tract and contribute to the pathophysiol. of IBS. Rearranged during transfection (RET) is a neuronal growth factor receptor tyrosine kinase critical for the development of the ENS as exemplified by Hirschsprung patients who carry RET loss-of-function mutations and lack normal colonic innervation leading to colonic obstruction. Similarly, RET signaling in the adult ENS maintains neuronal function by contributing to synaptic formation, signal transmission, and neuronal plasticity. Inhibition of RET in the ENS represents a novel therapeutic strategy for the normalization of neuronal function and the symptoms of IBS patients. Herein, we describe our screening effort and subsequent structure-activity relationships (SARs) in optimizing potency, selectivity, and mutagenicity of the series, which led to the discovery of a first-in-class, gut-restricted RET kinase inhibitor, 2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-N-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)acetamide (15, GSK3179106), as a clin. candidate for the treatment of IBS. GSK3179106 is a potent, selective, and gut-restricted pyridone hinge binder small mol. RET kinase inhibitor with a RET IC₅₀ of 0.3 nM and is efficacious in vivo.

ACS 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, HPLC of Formula: 76283-09-5.

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

Marton, Daniele published the artcilePreparation of Benzylstannanes by Zinc-Mediated Coupling of Benzyl Bromides with Organotin Derivatives. Physicochemical Characterization and Crystal Structures, Category: bromides-buliding-blocks, the publication is Organometallics (1996), 15(6), 1645-50, database is CAplus.

Benzyltrialkyl- and benzyltriphenylstannanes were easily prepared in a 1-pot synthesis via coupling reaction of benzyl bromide derivatives (C₆H₅CH₂Br and XYC₆H₃CH₂Br, X = H, Y = o-, m-, p-CH₃, o-, m-, p-F, o-, m-Cl, and p-Br; X = o-F, Y = p-Br) with R₃SnCl compounds (R = Et, Pr, Bu, and Ph) in THF/H₂O (NH₄Cl) medium mediated by Zn powder. Such coupling also occurs with (Bu₃Sn)₂O. Dibenzyldibutylstannane (15) was prepared by reaction of benzyl bromide with Bu₂SnCl₂ or (Bu₂SnCl)₂O, and (2-naphthylmethyl)tributylstannane (14) by reaction of 2-(bromomethyl)naphthalene with Bu₃SnCl. ¹³C- and ¹¹⁹Sn-NMR data are reported for all compounds, and Moessbauer data for the benzyltributylstannanes and benzyltriphenylstannanes. The crystal structures of Ph₃SnBn, with Bn = o- (17) and m-ClC₆H₅CH₂ (18) and o- (20) and m-FC₆H₅CH₂ (21) were determined

Organometallics 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

Chao, Rong published the artcileDesign, Semisynthesis, Insecticidal and Antibacterial Activities of a Series of Marine-Derived Geodin Derivatives and Their Preliminary Structure-Activity Relationships, Application In Synthesis of 76283-09-5, the publication is Marine Drugs (2022), 20(2), 82, database is CAplus and MEDLINE.

To enhance the biol. activity of the natural product geodin isolated from the marine-derived fungus Aspergillus sp., a series of new ether derivatives I [R = Et, 2-bromobenzyl, 2-chlorobenzyl, etc.] was designed and semisynthesized using a high-yielding one-step reaction. In addition, the insecticidal and antibacterial activities of all geodin congeners I were evaluated systematically. Most of these derivatives I showed better insecticidal activities against Helicoverpa armigera Hubner than Geodin. In particular, I [R = 2,3,4,5-tetrafluorobenzyl] showed potent insecticidal activity with an IC₅₀ value of 89μM, comparable to the pos. control azadirachtin (IC₅₀ = 70μM). Addnl., I [R = 2-chlorobenzyl, 2-fluorobenzyl, 3,5-difluorobenzyl, 2,3,4-trifluorobenzyl, 4-cyanobenzyl and 2-fluoro-3-chlorobenzyl] showed strong antibacterial activity against Staphylococcus aureus and Aeromonas salmonicida with MIC values in the range of 1.15-4.93μM. The preliminary structure-activity relationships indicated that the introduction of halogenated benzyl especially fluorobenzyl, into geodin and substitution of 4-OH was a key factors in increasing the insecticidal and antibacterial activities of geodin.

Marine Drugs 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

Fauber, Benjamin P. published the artcileDiscovery of 1-{4-[3-Fluoro-4-((3S,6R)-3-methyl-1,1-dioxo-6-phenyl-[1,2]thiazinan-2-ylmethyl)-phenyl]-piperazin-1-yl}-ethanone (GNE-3500): a Potent, Selective, and Orally Bioavailable Retinoic Acid Receptor-Related Orphan Receptor C (RORc or RORγ) Inverse Agonist, HPLC of Formula: 76283-09-5, the publication is Journal of Medicinal Chemistry (2015), 58(13), 5308-5322, database is CAplus and MEDLINE.

Retinoic acid receptor-related orphan receptor C (RORc, RORγ, or NR1F3) is a nuclear receptor that plays a major role in the production of interleukin (IL)-17. Considerable efforts have been directed toward the discovery of selective RORc inverse agonists as potential treatments of inflammatory diseases such as psoriasis and rheumatoid arthritis. Using the previously reported tertiary sulfonamide as a starting point, the authors engineered structural modifications that significantly improved human and rat metabolic stabilities while maintaining a potent and highly selective RORc inverse agonist profile. The most advanced δ-sultam compound I possessed favorable RORc cellular potency with 75-fold selectivity for RORc over other ROR family members and >200-fold selectivity over 25 addnl. nuclear receptors in a cell assay panel. The favorable potency, selectivity, in vitro ADME properties, in vivo PK, and dose-dependent inhibition of IL-17 in a PK/PD model support the evaluation of I in preclin. studies.

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, HPLC of Formula: 76283-09-5.

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

Kawanishi, T. published the artcileA Study of Boronic Acid Based Fluorescent Glucose Sensors, Product Details of C12H16BBrO2, the publication is Journal of Fluorescence (2004), 14(5), 499-512, database is CAplus and MEDLINE.

Boronic acid based anthracene dyes were designed, synthesized, and immobilized to solid phase, creating a continuous glucose sensor. Glucose sensitivities of dyes can decrease drastically after immobilization, therefore how to immobilize a dye to solid phase without changing the dye property is a key issue in developing the sensor. The glucose sensitivity of the simplest 1st generation sensor, which is based on an immobilized mono-phenylboronate/single-arm type, came short of the sensitivity requirement for practical use, because of the very moderate fluorescence intensity change over the physiol. glucose range. However, the 2nd generation, an immobilized bis-phenylboronate/double-arm type sensor, which contained two boronate groups in the dye moiety in expectation of a large intensity change, brought about considerable improvement on its glucose sensitivity. The authors tried to introduce functional groups onto an anthracene ring to improve the dyes’ fluorescence properties. Acetyl or carboxyl substitution on anthracene contributed to shift the fluorescence wavelength into the more visible range (red-shift) and a divergence of wavelength between an excitation peak and an emission peak. This improvement is advantageous to the design of an optical detection system. Furthermore, single arm immobilization to this carboxyl group, thus linking directly to the fluorophore led to a 3rd generation sensor, an immobilized bis-phenylboronate/single-arm type, that was twice as sensitive as that of the 2nd generation sensor, presumably due to increased mobility of the dye moiety. The results of the authors’ study advance closer toward a clin. useful continuous fluorescent glucose sensor.

Journal of Fluorescence published new progress about 166821-88-1. 166821-88-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester, name is 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C12H16BBrO2, Product Details of C12H16BBrO2.

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

Wang, Yan’en published the artcileTriazole-linked fluorescent bisboronic acid capable of selective recognition of the Lewis Y antigen, Formula: C12H16BBrO2, the publication is Bioorganic & Medicinal Chemistry Letters (2017), 27(9), 1983-1988, database is CAplus and MEDLINE.

Cell surface carbohydrates of the Lewis blood group antigens, Lewis X (Le^x), Lewis Y (Le^y), Lewis A (Le^a), and their sialylated derivatives, such as sialy Lewis X (sLe^x) and sialy Lewis A (sLe^a), play important roles in various recognition processes. These cell surface carbohydrates have also been associated with the development and progression of many types of cancers. Recently, we synthesized four anthracene-based fluorescent bisboronic acid sensors (compounds 2a-d) linked by ‘click’ chem. with tethers of different lengths to match the epitope of various Lewis group of sugars. Among the four compounds, 2a appears to have both high sensitivity and selectivity for Le^y among other carbohydrate antigens.

Bioorganic & Medicinal Chemistry Letters published new progress about 166821-88-1. 166821-88-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester, name is 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C15H21BO2, Formula: C12H16BBrO2.

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

Wang, Yan-En published the artcileSynthesis of fluorescent bisboronic acid sensors and their recognition of mono-/oligo-saccharides, COA of Formula: C12H16BBrO2, the publication is Chinese Chemical Letters (2017), 28(6), 1262-1267, database is CAplus.

Sensors capable of recognizing cell surface carbohydrates, such as sialyl Lewis X (sLe^x), are invaluable research tools and for the diagnosis and early detection of many forms of cancer. In this paper, we report the design and synthesis of a series of bisboronic acids 6(a-f) as fluorescent sensors towards mono-/oligosaccharides. Among them, compounds 6d and 6e showed strong binding affinities with glucose and fructose, while compound 6c, in which two anthracene-based boronic acid units were linked by a hexamethylene spacer, was able to recognize sLe^x selectivity and stained HEPG2 cells at 1 μmol/L.

Chinese Chemical Letters published new progress about 166821-88-1. 166821-88-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester, name is 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C15H21BO2, COA of Formula: C12H16BBrO2.

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