Tag: M.W=100-150

Verheijen, Jeroen C. published the artcileDiscovery of 4-Morpholino-6-aryl-1H-pyrazolo[3,4-d]pyrimidines as Highly Potent and Selective ATP-Competitive Inhibitors of the Mammalian Target of Rapamycin (mTOR): Optimization of the 6-Aryl Substituent, Name: (6-Hydroxypyridin-3-yl)boronic acid, the publication is Journal of Medicinal Chemistry (2009), 52(24), 8010-8024, database is CAplus and MEDLINE.

Design and synthesis of a series of 4-morpholino-6-aryl-1H-pyrazolo[3,4-d]pyrimidines, e.g. I, as potent and selective inhibitors of the mammalian target of rapamycin (mTOR) are described. Optimization of the 6-aryl substituent led to the discovery of inhibitors carrying 6-ureidophenyl groups, the first reported active site inhibitors of mTOR with subnanomolar inhibitory concentrations The data presented in this paper show that 6-arylureidophenyl substituents led to potent mixed inhibitors of mTOR and phosphatidylinositol 3-kinase α (PI3K-α), whereas 6-alkylureidophenyl appendages gave highly selective mTOR inhibitors. Combination of 6-alkylureidophenyl groups with 1-carbamoylpiperidine substitution resulted in compounds with subnanomolar IC₅₀ against mTOR and greater than 1000-fold selectivity over PI3K-α. In addition, structure based drug design resulted in the preparation of several 6-arylureidophenyl-1H-pyrazolo[3,4-d]pyrimidines, substituted in the 4-position of the arylureido moiety with water solubilizing groups. These compounds combined potent mTOR inhibition (IC₅₀ < 1 nM) with unprecedented activity in cellular proliferation assays (IC₅₀ < 1 nM).

Journal of Medicinal Chemistry published new progress about 903899-13-8. 903899-13-8 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Alcohol,Boronic Acids,Boronic acid and ester, name is (6-Hydroxypyridin-3-yl)boronic acid, and the molecular formula is C6H8O3, Name: (6-Hydroxypyridin-3-yl)boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Profft, E. published the artcileThe preparation of 4-halo-2-methylpyridines, SDS of cas: 18437-58-6, the publication is Journal fuer Praktische Chemie (Leipzig) (1959), 164-72, database is CAplus.

Diazotization of 2-methyl-4-aminopyridine (I) (Boekelheide, C.A. 49, 5256f) with HBr and NaNO₂ at -15°, decomposition of the diazonium salt by bringing slowly to room temperature, addition of aqueous NaOH, and steam distillation gave 72% 2-methyl-4-bromopyridine (II), b. 184°, b₁₄74-6°, n²⁰_D 1.5542. II treated with MeI in C₆H₆ 10 hrs. at room temperature gave the methiodide, m. 214° (decomposition); II picrate m. 186°. II, AcOH, and H₂O₂ gave 55% 2-methyl-4-bromopyridine N-oxide (III), b₁₄ 178°, also prepared from 2-methyl-4-nitropyridine N-oxide and HBr in an autoclave at 160° (Suzuki, C.A. 47, 8074b). III was reduced to II by powd. Fe in AcOH at 100°. II.HCl and Reinecke salt in H₂O gave on standing II reineckate, m. 152-3°. From I, dilute H₂SO₄, and NaNO₂ at -15°, followed by addition of cold aqueous KI, warming to room temperature, addition of NaOH, and extraction with Et₂O was obtained 52% 2-methyl-4-iodopyridine (IV), b₁₄ 84-6°, m. 42°; picrate, yellow, decomposed 209°; reineckate m. 156-7°; methiodide m. 238° (decomposition). IV, AcOH, and H₂O₂ gave 2-methyl-4-iodopyridine N-oxide, b₁₄ 192-4°. I with HBF₄ and NaNO₂ at -15° followed by warming, NaOH addition, and steam distillation gave 43% 2-methyl-4-fluoropyridine (V), b. 128-32°, n²⁰_D 1.4713, more easily soluble in H₂O than the Br and iodo analogs; V picrate m. 152°; reineckate m. 158-9°; methiodide m. 191°; N-oxide (made by both methods shown for III) b₁₄ 136-8°. IV (5 g.) refluxed at 210° with 10 g. powd. Cu gave a solid mass, which ground in a mortar, extracted with 2N HCl, the solution neutralized with NaOH, extracted with Et₂O, and the extract evaporated gave 52% 2,2′-dimethyl-4,4′-bipyridyl, yellowish, m. 83°; picrate, yellow, decompose 237°.

Journal fuer Praktische Chemie (Leipzig) published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C6H8N2, SDS of cas: 18437-58-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Fernandez, Estefania published the artcileBase-Controlled Heck, Suzuki, and Sonogashira Reactions Catalyzed by Ligand-Free Platinum or Palladium Single Atom and Sub-Nanometer Clusters, Category: pyridine-derivatives, the publication is Journal of the American Chemical Society (2019), 141(5), 1928-1940, database is CAplus and MEDLINE.

The assumption that oxidative addition is the key step during the cross-coupling reaction of aryl halides has led to the development of a plethora of increasingly complex metal catalysts, thereby obviating in many cases the exact influence of the base, which is a simple, inexpensive, and necessary reagent for this paramount transformation. Here, a combined exptl. and computational study shows that the oxidative addition is not the single kinetically relevant step in different cross-coupling reactions catalyzed by sub-nanometer Pt or Pd species, since the reactivity control is shifted toward subtle changes in the base. The exposed metal atoms in the cluster cooperate to enable an extremely easy oxidative addition of the aryl halide, even chlorides, and allow the base to bifurcate the coupling. With sub-nanometer Pd species, amines drive to the Heck reaction, carbonate drives to the Sonogashira reaction, and phosphate drives to the Suzuki reaction, while for Pt clusters and single atoms, good conversion is only achieved using acetate as a base. This base-controlled orthogonal reactivity with ligand-free catalysts opens new avenues in the design of cross-coupling reactions in organic synthesis.

Journal of the American Chemical Society published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C5H6BNO2, Category: pyridine-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Felts, Andrew S. published the artcileDiscovery of VU0409106: A negative allosteric modulator of mGlu₅ with activity in a mouse model of anxiety, Recommanded Product: 4-Amino-2-picoline, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(21), 5779-5785, database is CAplus and MEDLINE.

Development of SAR in an aryl ether series of mGlu₅ NAMs leading to the identification of tool compound VU0409106 is described in this Letter. VU0409106 is a potent and selective neg. allosteric modulator of mGlu₅ that binds at the known allosteric binding site and demonstrates good CNS exposure following i.p. dosing in mice. VU0409106 also proved efficacious in a mouse marble burying model of anxiety, an assay known to be sensitive to mGlu₅ antagonists as well as clin. efficacious anxiolytics.

Bioorganic & Medicinal Chemistry Letters published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C6H8N2, Recommanded Product: 4-Amino-2-picoline.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Zurwerra, Didier published the artcileSynthesis and Stability of Boratriazaroles, Safety of 2-Pyridinylboronic acid, the publication is Organic Letters (2015), 17(1), 74-77, database is CAplus and MEDLINE.

We describe the synthesis and stability anal. of novel boratriazaroles that can be viewed as bioisosteres of imidazoles or pyrazoles. These heterocycles could conveniently be obtained by condensing a boronic acid and amidrazone 1 in various solvents. A detailed stability anal. of selected compounds at different pH values as a function of time led to the identification of steric hindrance around the boron atom as a key element for stabilization.

Organic Letters published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C10H9ClN2O, Safety of 2-Pyridinylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Bhaskar, Boyapally published the artcileTamarindus indica seed ash extract for C-C coupling under added organics and volatile organic solvent-free conditions: a waste repurposing technique for Suzuki-Miyaura reaction, COA of Formula: C5H6BNO2, the publication is Environmental Science and Pollution Research, database is CAplus and MEDLINE.

A tremendous research has been appeared on Pd-catalyzed Suzuki-Miyaura cross-coupling (SMC) during the last four decades due to its high prominence in constructing biaryl motifs of several complexes as well as simple organic compounds of high biol. and com. significance. The use of organic solid waste-derived materials for SMC in benign solvents like water/aqueous media is a very good achievement in these cases. We report in this article the usability of water extract of Tamarindus indica seeds ash (WETS) as a renewable base and reaction medium for Pd(OAc)₂-catalyzed SMC reaction at room temperature (RT). The WETS has been characterized using powder XRD, EDAX, SEM, and FTIR anal. Furthermore, this process is highly environmentally beneficial by the waste repurposing to prominent chem. transformation along with the advantages such as ambient condition and avoids non-renewable chems. like volatile organic solvents, ligands, promoters, and bases. Based on these merits and the quick reactions with high yields of products, this method can attain the interest of the scientific community in exploring the waste-derived ashes to significant chem. transformations.

Environmental Science and Pollution Research published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C5H6BNO2, COA of Formula: C5H6BNO2.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Lakshmidevi, Jangam published the artcileA quick and low E-factor waste valorization procedure for CuCl-catalyzed oxidative self-coupling of (hetero)arylboronic acid in pomegranate peel ash extract, Category: pyridine-derivatives, the publication is Green Chemistry Letters and Reviews (2022), 15(3), 538-545, database is CAplus.

The application of waste biomass-derived materials to synthetic chem. is a remarkable achievement, and the use of aqueous media is further advancement. The switch towards earth’s abundant metals like cobalt/copper/iron/nickel from precious palladium in C-C coupling reactions is also a high throughput in the global sustainability perspective. Herein, we describe a CuCl-catalyzed homocoupling of (hetero)arylboronic acids (HABAs) in water extract of pomegranate ash (WEPA) with low E-factor of 1.25 without including the column chromatog. separation of products, which helped in understanding the effectiveness of this method on comparison to reported protocols lacking amounts of silica gel and eluents, however, it was 171.64 by including column purification The reactions are conducted at room temperature to deliver self-coupling products with 90-99% yields in 10-45 min under precious metal, ligand, non-renewable base, toxic/problematic organic solvent and added oxidant-free conditions. A wide range of substrates were screened with aryl and heteroaryl moieties containing diversified functional groups. The substitution of earth’s rare metals-based catalysts by abundant copper, exploration of waste to state-of-the-art C-C coupling, use of biorenewable base, aqueous media, ambient conditions, operational simplicity, excellent yields of biaryls and quick reactions are the noteworthy advantages of this protocol.

Green Chemistry Letters and Reviews published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C5H6BNO2, Category: pyridine-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Rao, H. Surya Prakash published the artcileCopper-catalyzed C(sp³)-C(sp²) cross-coupling. Synthesis of 4-aryl-2-alkyl-amino-3-nitro-4H-chromenes, COA of Formula: C5H6BNO2, the publication is European Journal of Organic Chemistry (2014), 2014(17), 3646-3655, database is CAplus.

Inexpensive copper(II) acetate effectively catalyzes cross-coupling of electron-deficient as well as electron-rich arylboronic acids with 4-methylsulfanyl-2-alkylamino-3-nitro-4H-chromenes under near neutral conditions at room temperature to furnish a range of 4-aryl-4H-chromenes. This new strategy enabled substitution of the C(4)SMe group present on a sp³ hybridized carbon of the 4H-chromenes with aryl/heteroaryl groups. Mechanistic probing revealed that the Cu(I)-Cu(III) cycle is involved in catalysis. One-pot sequential substitution of C(4)SMe followed by C(6)Br with aryl groups was achieved through Cu(OAc)₂ and Pd₂(dba)₃ (Suzuki coupling) catalysis. © 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

European Journal of Organic Chemistry published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C5H6BNO2, COA of Formula: C5H6BNO2.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Sundar, Ch. Syama published the artcileThe synthesis and bioactivity of dimethyl (2,3-dihydrobenzo[b][1,4]dioxin-6-yl)(arylamino)methylphosphonates, Synthetic Route of 18437-58-6, the publication is Phosphorus, Sulfur and Silicon and the Related Elements (2014), 189(4), 551-557, database is CAplus.

A new series of α-amino phosphonates I (R = aryl) were synthesized by a one-pot, three-component reaction of 2,3-dihydrobenzo[b][1,4]dioxine-6-carboxaldehyde, primary aromatic amines, and HP(O)(OMe)₂ by using nano-TiO₂ as a catalyst under solvent-free conditions at 50°. Major advantages of the method are high yields, short reaction times, recyclable catalyst, and solvent-free reaction conditions. Among these novel α-amino phosphonates, I (R = 3-O₂NC₆H₄, 4-FC₆H₃-3-NO₂) showed higher antioxidant activity in DPPH scavenging, reducing power assay, and lipid peroxidation

Phosphorus, Sulfur and Silicon and the Related Elements published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C9H17NO, Synthetic Route of 18437-58-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Sivudu, K. Samba published the artcileHighly efficient and reusable hydrogel-supported nano-palladium catalyst: Evaluation for Suzuki-Miyaura reaction in water, Application of 2-Pyridinylboronic acid, the publication is Journal of Molecular Catalysis A: Chemical (2008), 295(1-2), 10-17, database is CAplus.

Ligand-free, palladium-supported, poly(N-isopropylacrylamide-co-potassium methacrylate) [poly(NIPA-co-PMA)] hydrogel nanocomposite with different comonomer ratios were synthesized. The developed hydrogel-palladium composites were characterized by SEM, TEM, UV-vis DRS and x-ray diffraction. The catalytic performance of these hydrogel-palladium nanocomposites was examined for Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acids in an aqueous medium. The hydrogel with comonomer ratio of 8.8:1.6 mmol of NIPA:PMA exhibited optimum catalytic activity, which can be effectively reused 5-6 times without loss of catalytic activity.

Journal of Molecular Catalysis A: Chemical published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C7H5Cl2NO, Application of 2-Pyridinylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem