Tag: M.W=200-250

Gottumukkala, Aditya L. published the artcileEfficient Formation of Benzylic Quaternary Centers via Palladium Catalysis, HPLC of Formula: 480438-56-0, the publication is ChemSusChem (2013), 6(9), 1636-1639, database is CAplus and MEDLINE.

Pd(O₂CCF₃)₂ and 2,2-bipyridine catalyzed the formation of benzylic quaternary centers from arylboronic acids and β-disubstituted enones. For cyclic substrates, only 1 mol% of palladium is required for full conversion, and a variety of arylboronic acids could be reacted with yields exceeding 90%. 5-Membered cyclic enones were found to be most reactive, followed by 6-membered rings and then 7-membered rings. E.g., reaction of 3-methyl-2-cyclohexenone and PhB(OH)₂ gave 92% I. In the case of acyclic substrates, e.g. (E)-Me₃COCH₂CMe:CHCOMe, 5 mol% Pd was found to be necessary, along with the addition of 20 mol% KSbF6 to afford the highest conversion.

ChemSusChem published new progress about 480438-56-0. 480438-56-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 3-Chloro-4-isopropoxyphenylboronic acid, and the molecular formula is C9H12BClO3, HPLC of Formula: 480438-56-0.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Arai, Junya published the artcileChemoprevention for Colorectal Cancers: Are Chemopreventive Effects Different Between Left and Right Sided Colorectal Cancers?, Application In Synthesis of 637-07-0, the publication is Digestive Diseases and Sciences, database is CAplus and MEDLINE.

Recent studies have suggested that right- and left-sided colorectal cancers (CRCs) are molecularly distinct. In this study, we examined the association between the risk of right- and left-sided CRC and drug use to estimate their chemopreventive effects .This multicenter retrospective cohort study was conducted using the data of hospitalized patients between 2014 and 2019 from nine hospital databases. The primary outcomes were right- and left-sided CRC. We evaluated the association of CRCs with drug use and clin. factors. Odds ratios adjusted for age, sex, Charlson Comorbidity Index scores, and smoking status were calculated We also compared the transcriptional profiling in precancerous lesions, including sessile serrated lesions (SSLs). A total of 307,938 patients, including 2745 with right-sided CRC and 4819 with left-sided CRC, were analyzed. The use of nonsteroidal anti-inflammatory drugs (NSAIDs), aspirin, cyclooxygenase-2 inhibitors, and steroids was associated with a lower risk of both right- and left-sided CRCs. In contrast, statins, other lipid-lowering agents, and metformin were associated with a lower risk of left-sided CRC. Transcriptomic anal. showed that SSL, which predominantly develops in the right colon, was associated with a lower expression of lipid metabolism-related genes. Targeting lipid metabolism may be useful for chemoprevention of left-sided CRCs, while development of right-sided CRCs may be independent of this pathway.

Digestive Diseases and Sciences published new progress about 637-07-0. 637-07-0 belongs to chlorides-buliding-blocks, auxiliary class Inhibitor,Cell Cycle,PPAR, name is Ethyl 2-(4-chlorophenoxy)-2-methylpropanoate, and the molecular formula is C12H15ClO3, Application In Synthesis of 637-07-0.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Schroeter, G. published the artcileHydrogenated naphthalenes and their transformations. III. Tetrahydronaphthalenesulfonic acids, tetrahydronaphthols and their derivatives, HPLC of Formula: 61551-49-3, the publication is Justus Liebigs Annalen der Chemie (1922), 83-160, database is CAplus.

2-Tetralinsulfonic acid (tetrahydronaphthalene-2-sulfonic acid),formed by the action of concentrated H₂SO₄ upon C₁₀H₁₂, seps. with 2 H₂O from H₂SO₄, m. 75°. Sodium salt, glistening leaflets with 1 H₂O; barium salt, leaflets; lead salt,with 1 H₂O, small leaflets. Ammonium salt, glistening leaflets Chloride, plates, b₁₈ 197-200°, m. 58°. With NH₃ it yields the amide, m. 135-7°, and with PhNH₂, the anilide, m. 155-6°. The mixture of acids obtained when the sulfonation is carried out with ClSO₃H may be separated by crystallization of the acids from CHCl₃, the 1-acid separating first, or by precipitating the Pb salt of the 1-acid with Pb(OAc)₂ or by crystallizing the 2-amide from NaOH. 1-Tetralinsulfonic acid: lead salt, glistening leaflets with 3H₂O; sodium salt, leaflets with 2 H₂O, and barium salt, 3 H₂O. Amide, leaflets, m. 139-40°;chloride, m. 70-2°; anilide, m. 148-9°. Upon reduction of the chloride mixture with Zn dust, the tetralylthiols result. 2-Tetralylthiolacetic acid, by the reaction of ClCH₂CO₂Na upon C₁₀H₁₁SNa, needles, m. 78-80°. Ammonium salt, glistening leaflets. Concentrated H₂SO₄gives a greenish yellow color; on boiling the dilute solution and making alk. with NaOH, sodium bis-ar-tetrahydrothionaphthenedisulfonate is precipitated as fine steel-blue needles with Cu luster. The 1-thiolacetic acid crystallizes in glistening plates, m. 133-5°. Whenα-C₁₀H₇OH is reduced with H at 200°in the presence of Ni, the product consists of about 10% ofα-ketotetrahydronaphthalene, 25-30 %C₁₀H₁₁OH and a large quantity of C₁₀H₁₂. At low temperatures the ketone is the main product. In the reduction of the ketone with Na and EtOH, it yields ac-C₁₀H₁₁OH. ac-β-C₁₀H₁₁OH is the principal product of the catalytic reduction of β-C₁₀H₇OH. The SO₃H acids are therefore valuable starting points in the production of C₁₀H₁₁OH, which are formed by fusion with alkalies. These are called tetralols. 2-Tetralolmethyl ether, by the action of Me₂SO₄ in NaOH, b₁₁ 129-31°; acetate, rather viscous oil,b₁₄ 158°; benzoate, prisms, b₁₀220-2°, m. 96°. 2-Tetralol-3-sulfonic acid, by warming in concentrated H₂SO₄ until soluble in H₂O,needles, with 2 H₂O, m. 92°. The sodium and barium salts are difficultly soluble With diazo solutions it couples to form strongly colored azo dyes. Methoxy derivative, from C₁₀H₁₁OMe and concentrated H₂SO₄, m. 107°. 1-Bromo-2-tetralol, by the direct action of Br in CCl₄, b₁₃160°, m. 74°; also prepared by desulfonation of 1-bromo-2-tetralol-3-sulfonic acid (sodium salt, with 3H₂O) with HCl. This has a greater toxic effect upon bacteria than lysol or PhOH. 1,3-Dibromo-2-tetralol,b₁₂ 198-201°, m. 37°. Acetate, m. 87°, is the best means of purification. 1-Bromo-3-nitro-2-tetralol, by the action of HNO₃ on the SO₃H derivative, long yellow needles, m. 129°. Sodium salt, glistening red leaflets,which color wool a light orange shade. Methyl ether, yellow needles, m. 64°. 1-Chloro-3-nitro-2-tetralol, yellow needles,m. 96°. 1-Bromo-3-amino-2-tetralol, by reduction of the NO₂ derivative with SnCl₂ in Et₂O saturated with HCl, fine needles, m. 127° (hydrochloride, sulfate and nitrate sparingly soluble in cold H₂O); methyl ether,isolated as the sulfate, long needles with 4 H₂O. 3-Amino-2-tetralol (A) is also formed in the above reduction and forms leaflets, m. 202°. Its hydrochloride and nitrate are easily soluble in H₂O, while the sulfate is difficultly soluble Carbonyl-3,2-aminotetralol,C₁₀H₁₀.NH.CO.O by heating the azide in C₇H₈, m. 196°, also forms A when heated with concentrated HCl in a sealed tube. With piperonal A gives piperonylidene-3,2-aminotetratol, yellow, m. 160°; with alk. Me₂SO₄ it yields piperonylidene-3,2-aminotetralol methyl ether, m. 120°. With dilute HCl this yields the methyl ether of A, large leaflets, m.86°. 1-Amino-2-tetralol (B), obtained by coupling 2-C₁₀H₁₁OH with sulfanilic acid diazide and reducing with SnCl₂ or from 1-benzeneazo-2-tetralol(red, m. 84°; monobromo derivative m. 204°) with Na₂S₂O₄, leaflets, m. 148°. An isomer, m. 173°, is sometimes obtained which gives a carbonyl-aminotetralol, red needles, m. 188°. Carbonyl-1-amino-2-tetralol, m. 189-90°. Methyl ether of B, m.64°, is obtained by reducing 1,2-O₂NC₁₀H₆OMe with SnCl₂, isolating the product and reducing this with Na and AmOH, and yields B upon heating with HCl in a sealed tube. 1,3-Nitrotetralinsulfonic acid, obtained by the action of concentrated H₂SO₄ on 1-C₁₀H₁₁NO₂, forms an amide m.189°, and upon reduction with SnCl₂ and excess of HCl, or Fe and HCl, gives 1-aminotetralin-3-sulfonic acid (C),leaflets. When a mixture of the 1- and 2-NO₂ derivatives is sulfonated, 2-nitrotetralin-4-sulfonic acid is also formed, the amide of which m. 211-2°, and which yields 2-aminotetralin-4-sulfonic acid on reduction, the hydrochloride of which is soluble in 120 parts H₂O. The action of alkalies on C gives, as the main product, AcNHC₁₀H₁₁. 4-Acetamino-2-tetralol is obtained by heating the diazo solution from 4,2-AcNHC₁₀H₁₀NH₂, m. 222°,and, on saponification, gives 4-amino-2-tetralol, leaflets, m. 177°. 1,3-Dinitro-2-tetralol, pale yellow needles, m. 141°. Sodium salt, orange-yellow; potassium salt, orange-yellow; ammonium salt,citron-yellow; barium and lead salts. The 1st 2 salts change color on heating and explode at 180-90°, while the last 3 do not change color and burn quietly on heating. Methyl ether (D), from MeNaSO₄ and(O₂N)₂C₁₀H₉ONa in C₇H₈, needles, m. 86.5°. Reduced with SnCl₂ in Et₂O, 1-nitro-3-amino-2-tetralol results, Cu-colored needles, m. 127°. Hydrochloride, pale yellow leaflets. Methyl ether, by the reduction of D, yellow leaflets, m. 117°. Hydrochloride, sparingly soluble in HCl, but decomposed by H₂O. Reduced with SnCl₂ in EtOH,1,3-diamino-2-tetralol is formed, leaflets, m. 214-6°. Methyl ether, prisms, m. 89°. Heated under pressure with CO₂ in the presence of alkalies,2-C₁₀H₁₁OH gives 2,3-tetralsalicylic acid, m.182°; sodium and calcium salts. Methyl ester, b₁₅179°, m. 42°. Ethyl ester, b₁₃ 179°. 2-Tetralol-3-carbonic hydrazide, m. 146°. Acetonehydrazone, m.235°. Azide, long needles, m. 99-100°. Anilide, m.182-4°. 2,3-Acetyltetralol-carboxylic acid, m. 142-3°. 1-Nitro-2-tetralol-3-carboxylic acid, yellow needles, m.200-2°, which may be reduced to the 1-amino derivative, prisms,m. 208-10°; the hydrochloride is sparingly soluble in HCl and the diacetate m. 180-1°. 4-Amino-1-tetralol, needles m. 146-7°, may be obtained by reducing p-ONC₁₀H₁₀OH with SnCl₂, or 1-tetralol-4-azobenzene-4′-sulfonic acid, red dye, by means of alk. Na₂S₂O₄. Ethyl ether (Ber. 31, 898), by reduction of EtOC₁₀H₁₀N₂ Ph with H, m. 60°,and gives p-ethoxytetralylurea, m. 240-1°. 2-Amino-1-tetralol, m. 110-1°, gives with urea an oxazolone, m. 205°. 3-Acetamino-1-tetralol, from the diazo compound, needles, m.211°. 3-Amino-1-tetralol, leaflets, m. 197°;hydrochloride, needles. With K₂CO₃ and CO₂ this gives 1,2-tetralsalicylic acid, m. 165-6°,the sodium salt of which crystallizes as leaflets with 3H₂O. Acetate, m. 170°. Methyl ester,b₁₆ 190°, m. 56°. Hydrazide, long needles, m.205°. Acetonehydrazone, m. 136°. Azide, m. 84°.

Justus Liebigs Annalen der Chemie published new progress about 61551-49-3. 61551-49-3 belongs to chlorides-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 5,6,7,8-Tetrahydronaphthalene-2-sulfonyl chloride, and the molecular formula is C10H11ClO2S, HPLC of Formula: 61551-49-3.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Anderson, Thomas F. published the artcileBis(2-thienyl)silanes: new, versatile precursors to arylsilanediols, Recommanded Product: Dichloro(methyl)(octyl)silane, the publication is Tetrahedron Letters (2006), 47(20), 3353-3355, database is CAplus.

Silanediols are effective bioisosteres for the hydrated carbonyl group. Current methods for the formation of silanediols place a number of constraints on how and where this functionality may be used. A range of arylsilanes that would allow both the formation of arylsilanediols and that are also compatible with multi-step synthetic routes, were studied as possible precursors to silanediols. Through this study bis(2-furyl)silanes and, in particular, bis(2-thienyl)silanes were identified as practical precursors to arylsilanediols.

Tetrahedron Letters published new progress about 14799-93-0. 14799-93-0 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is Dichloro(methyl)(octyl)silane, and the molecular formula is C9H20Cl2Si, Recommanded Product: Dichloro(methyl)(octyl)silane.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Min, Kyung-Lyum published the artcileSynthesis and differential properties of creatine analogs as inhibitors for human creatine kinase isoenzymes, Related Products of chlorides-buliding-blocks, the publication is European Journal of Biochemistry (1996), 238(2), 446-452, database is CAplus and MEDLINE.

Fourteen new creatine analogs, all with a guanidine function and either a polar or an apolar group instead of the creatine carboxylic function, were tested as potential inhibitors for human creatine kinase by kinetic anal. of their effects on the reaction rate. Only compounds bearing an apolar aromatic moiety, which was spaced from the guanidine function by at least two bonds, proved to have a significant inhibitory activity and showed a mixed-type inhibition similar to that of creatine. Among these compounds, 2,6-dichlorobenzylguanidine (K_i = 5.6 mM and 39.8 mM for muscle-type and brain-type creatine kinases, resp.) and 3-(2,6-dichlorophenyl)propylguanidine (K_i = 15 mM and 4.5 mM) were the more potent inhibitors and showed a significant isoenzyme selectivity between muscle- and brain-type creatine kinases. Our results are in agreement with recent data that suggest the location of a hydrophobic pocket near the guanidine-binding domain of the enzyme. The observed selectivity in isoenzyme inhibition may be useful to study structural differences in catalytic centers.

European Journal of Biochemistry published new progress about 51656-68-9. 51656-68-9 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene, name is 3-(2,6-Dichlorophenyl)propanoic acid, and the molecular formula is C9H8Cl2O2, Related Products of chlorides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Zhang, Chun-Hui published the artcilePotent noncovalent inhibitors of the main protease of SARS-CoV-2 from molecular sculpting of the drug perampanel guided by free energy perturbation calculations, Safety of (3-Chloro-5-propoxyphenyl)boronic acid, the publication is ACS Central Science (2021), 7(3), 467-475, database is CAplus and MEDLINE.

Starting from our previous finding of 14 known drugs as inhibitors of the main protease (M^pro) of SARS-CoV-2, the virus responsible for COVID-19, we have redesigned the weak hit perampanel to yield multiple noncovalent, nonpeptidic inhibitors with ca. 20 nM IC₅₀ values in a kinetic assay. Free-energy perturbation (FEP) calculations for M^pro-ligand complexes provided valuable guidance on beneficial modifications that rapidly delivered the potent analogs. The design efforts were confirmed and augmented by determination of high-resolution X-ray crystal structures for five analogs bound to M^pro. Results of cell-based antiviral assays further demonstrated the potential of the compounds for treatment of COVID-19. In addition to the possible therapeutic significance, the work clearly demonstrates the power of computational chem. for drug discovery, especially FEP-guided lead optimization.

ACS Central Science published new progress about 1256345-74-0. 1256345-74-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Chloro-5-propoxyphenyl)boronic acid, and the molecular formula is C8H5F3O2S, Safety of (3-Chloro-5-propoxyphenyl)boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Jiang, Yuan published the artcileSynthesis and antifungal evaluation of phenol-derived bis(indolyl)methanes combined with FLC against Candida albicans, Category: chlorides-buliding-blocks, the publication is Bioorganic & Medicinal Chemistry Letters (2022), 128525, database is CAplus and MEDLINE.

In this work, it was focused on boron trifluoride etherate catalyzed condensation of indole and salicylaldehydes RCHO (R = 2-hydroxyphenyl, 4-(dimethylamino)-2-hydroxyphenyl, 3,5-dibromo-2-hydroxyphenyl, etc.) to form bis(indolyl)methanes (BIMs) I in high yields, and in vitro antifungal activity against Candida albicans were evaluated. The results showed that most phenol-derived BIMs I combined with fluconazole (FLC) exhibited good antifungal activity against sensitive and drug-resistant C. albicans. Further mechanism study demonstrated that I (R = 3-bromo-2-hydroxyphenyl) combined with FLC could inhibit hyphal growth, result in ROS accumulation, and decrease mitochondrial membrane potential (MMP) as well as altering membrane permeability.

Bioorganic & Medicinal Chemistry Letters published new progress about 19652-33-6. 19652-33-6 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Bromide,Benzene,Phenol,Aldehyde, name is 5-Bromo-3-chloro-2-hydroxybenzaldehyde, and the molecular formula is C7H4BrClO2, Category: chlorides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Wu, Lili published the artcileChiral thiourea catalyzed asymmetric Henry reaction: construction of stereogenic center bearing a CF₃ group from 2,2,2-trifluoroacetophenone substrates, SDS of cas: 5860-95-7, the publication is Youji Huaxue (2017), 37(4), 936-942, database is CAplus.

An asym. Henry reaction with 2,2,2-trifluoroacetophenone as trifluoromethyl building block was described. This reaction was catalyzed by bifunctional thiourea derived from quinine to give the product bearing a CF₃ stereogenic center in good yield with good enantioselectivity.

Youji Huaxue published new progress about 5860-95-7. 5860-95-7 belongs to chlorides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Chloride,Benzene,Ketone, name is 1-(2-Chlorophenyl)-2,2,2-trifluoroethanone, and the molecular formula is C24H12, SDS of cas: 5860-95-7.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Chen, Xiao-Yang published the artcilePd-Catalyzed, ortho C-H Methylation and Fluorination of Benzaldehydes Using Orthanilic Acids as Transient Directing Groups, Synthetic Route of 929621-33-0, the publication is Journal of the American Chemical Society (2018), 140(8), 2789-2792, database is CAplus and MEDLINE.

The direct, Pd-catalyzed ortho C-H methylation and fluorination of benzaldehydes have been accomplished using com. available orthanilic acids as transient directing groups. In these reactions, the 1-fluoro-2,4,6-trimethylpyridinium salts can be either a bystanding F⁺ oxidant or an electrophilic fluorinating reagent. An X-ray crystal structure of a benzaldehyde ortho C-H palladation intermediate was obtained using triphenylphosphine as the stabilizing ligand.

Journal of the American Chemical Society published new progress about 929621-33-0. 929621-33-0 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Bromide,Benzene,Aldehyde, name is 4-Bromo-2-chloro-6-fluorobenzaldehyde, and the molecular formula is C7H3BrClFO, Synthetic Route of 929621-33-0.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Zhang, Chun-Hui published the artcileOptimization of triarylpyridinone inhibitors of the main protease of SARS-CoV-2 to low-nanomolar antiviral potency, SDS of cas: 1256345-74-0, the publication is ACS Medicinal Chemistry Letters (2021), 12(8), 1325-1332, database is CAplus and MEDLINE.

Non-covalent inhibitors of the main protease (M^pro) of SARS-CoV-2 having a pyridinone core were previously reported with IC₅₀ values as low as 0.018μM for inhibition of enzymic activity and EC₅₀ values as low as 0.8μM for inhibition of viral replication in Vero E6 cells. The series has now been further advanced by consideration of placement of substituted five-membered-ring heterocycles in the S4 pocket of M^pro and N-methylation of a uracil ring. Free energy perturbation calculations provided guidance on the choice of the heterocycles, and protein crystallog. confirmed the desired S4 placement. Here we report inhibitors with EC₅₀ values as low as 0.080μM, while remdesivir yields values of 0.5-2μM in side-by-side testing with infectious SARS-CoV-2. A key factor in the improvement is enhanced cell permeability, as reflected in PAMPA measurements. Compounds 19 (I) and 21 (II) are particularly promising as potential therapies for COVID-19, featuring IC₅₀ values of 0.044-0.061μM, EC₅₀ values of ca. 0.1μM, good aqueous solubility, and no cytotoxicity.

ACS Medicinal Chemistry Letters published new progress about 1256345-74-0. 1256345-74-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Chloro-5-propoxyphenyl)boronic acid, and the molecular formula is C18H34N4O5S, SDS of cas: 1256345-74-0.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics