Month: November 2022

Elumalai, Nagarajan published the artcileNanomolar Inhibitors of the Transcription Factor STAT5b with High Selectivity over STAT5a, Formula: C10H10O6, the publication is Angewandte Chemie, International Edition (2015), 54(16), 4758-4763, database is CAplus and MEDLINE.

Src homol. 2 (SH2) domains play a central role in signal transduction. Although many SH2 domains have been validated as drug targets, their structural similarity makes development of specific inhibitors difficult. The cancer-relevant transcription factors STAT5a and STAT5b are particularly challenging small-mol. targets because their SH2 domains are 93% identical on the amino acid level. Here the authors present the natural product-inspired development of the low-nanomolar inhibitor I, as the first small mol. which inhibits the STAT5b SH2 domain (K_i=44 nM) with more than 50-fold selectivity over STAT5a. The binding site of the core moiety of I was validated by functional anal. of point mutants. A prodrug of I was shown to inhibit STAT5b with high selectivity over STAT5a in tumor cells. I provides the first demonstration that naturally occurring SH2 domains with more than 90% sequence identity can be selectively targeted with small organic mols.

Angewandte Chemie, International Edition published new progress about 5411-14-3. 5411-14-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2,2-(1,2-Phenylenebis(oxy))diacetic acid, and the molecular formula is C10H10O6, Formula: C10H10O6.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Huckins, John R. published the artcileRh(III)-Catalyzed C-H Activation and Double Directing Group Strategy for the Regioselective Synthesis of Naphthyridinones, Synthetic Route of 1293990-73-4, the publication is Journal of the American Chemical Society (2013), 135(39), 14492-14495, database is CAplus and MEDLINE.

A general Rh-(III)-catalyzed synthesis of naphthyridinone derivatives is described. It relies on a double-activation and directing approach leveraging nicotinamide N-oxides as substrates. In general, high yields and selectivities can be achieved using low catalyst loadings and mild conditions (room temperature) in the couplings with alkynes, while alkenes require slightly more elevated temperatures

Journal of the American Chemical Society published new progress about 1293990-73-4. 1293990-73-4 belongs to catalysis-chemistry, auxiliary class Aliphatic Chain, name is O-Pivaloylhydroxylamine trifluoromethanesulfonate, and the molecular formula is C6H12F3NO5S, Synthetic Route of 1293990-73-4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Kay, John E. published the artcileDirect effects of 1,3-diaminopropane on reticulocyte lysate protein synthesis, SDS of cas: 10517-44-9, the publication is FEBS Letters (1980), 121(2), 309-12, database is CAplus and MEDLINE.

1,3-Diaminopropane-2HCl (I) [10517-44-9] inhibited protein synthesis by reticulocyte lysates in the presence of 2 mM Mg²⁺. This was apparently a simple cation effect, since I itself supported protein synthesis by the system in the absence of normal divalent cations. The inhibitory action of I was not due to an antagonistic effect toward spermidine, a natural polyamine associated with protein synthesis, because the inhibition was not diminished when the lyzate was supplemented with large amounts of spermidine-HCl [334-50-9]. Direct inhibition of protein synthesis by I would include, among other effects, a reduction in the concentration of enzymes required for polyamine synthesis. This raises questions as to the specificity of I as an inhibitor of polyamine formation.

FEBS Letters published new progress about 10517-44-9. 10517-44-9 belongs to catalysis-chemistry, auxiliary class Salt,Amine,Aliphatic hydrocarbon chain, name is Propane-1,3-diamine dihydrochloride, and the molecular formula is C3H12Cl2N2, SDS of cas: 10517-44-9.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Klingebiel, Uwe published the artcileCycloaddition reactions of aminofluorosilanes, SDS of cas: 312-40-3, the publication is Journal of Organometallic Chemistry (1978), 144(3), 381-8, database is CAplus.

[2+2] Cycloaddition reaction of RR¹FSiNHR² with BuLi gave 70-80% I (R = Me, Ph; R¹ = Me, MeEtCH, Ph; R² = Me₂CH, Me₃C, 2,4,6-Me₃C₆H₂) (5 compounds). RR¹FSiNHR² were prepared in 70-90% yields by treating RR¹SiF₂ with LiNHR².

Journal of Organometallic Chemistry published new progress about 312-40-3. 312-40-3 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Difluorodiphenylsilane, and the molecular formula is C12H10F2Si, SDS of cas: 312-40-3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Guan, Renpeng published the artcileDecarboxylative oxygenation of carboxylic acids with O₂via a non-heme manganese catalyst, Related Products of catalysis-chemistry, the publication is Green Chemistry (2022), 24(7), 2946-2952, database is CAplus.

Decarboxylative oxygenation of carboxylic acids using a non-heme manganese catalyst under blue light irradiation with O₂ as the sole oxidant. Featuring mild reaction conditions, the protocol allowed readily available carboxylic acids to be converted into a wide variety of valuable aldehydes, ketones and amides. Mechanistic studies indicated that the decarboxylation and oxygenation involved the formation of active Mn-oxygen species.

Green Chemistry published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Related Products of catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Neggad, Abdelhamid published the artcileA new method of extracting polyphenols from honey using a biosorbent compared to the commercial resin amberlite XAD2, Safety of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is Journal of Separation Science (2021), 44(10), 2089-2096, database is CAplus and MEDLINE.

A new extraction method of polyphenols from honey using a biodegradable resin was developed and compared with the common com. resin amberlite XAD2. For this purpose, three honey samples of Algerian origin were selected for the different physicochem. and biochem. parameters study. After extraction of the target compounds by both resins, the polyphenol content was determined, the antioxidant activity was tested, and liquid chromatog.-mass spectrometry analyses were performed for identification and quantification. The results showed that physicochem. and biochem. parameters meet the norms of the International Honey Commission, and the H1 sample seemed to be of high quality. The optimal conditions of extraction by biodegradable resin were a pH of 3, an adsorption dose of 40 g/L, a contact time of 50 min, an extraction temperature of 60°C, and no stirring. The regeneration and reuse number of both resins was three cycles. The polyphenol contents demonstrated a higher extraction efficiency of biosorbent than of XAD2, especially in H1. Liquid chromatog.-mass spectrometry analyses allowed for the identification and quantification of 15 compounds in the different honey samples extracted using both resins and the most abundant compound was 3,4,5-trimethoxybenzoic acid. In addition, the biosorbent extracts showed stronger antioxidant activities than the XAD2 extracts

Journal of Separation Science published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C11H12O4, Safety of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

shirali, Somayeh published the artcilePreparation and characterization of novel hybrid nanomaterial catalyst MCM-41@AzaCrown-SB-Cu and its application in synthesis of 1, 2, 3-triazole derivatives in click chemistry, HPLC of Formula: 5411-14-3, the publication is Journal of Porous Materials (2020), 27(6), 1601-1611, database is CAplus.

Synthesis of efficient and reusable catalyst was carried out by immobilization of azacrown ether onto the covalently linked amine-functionalized mesoporous MCM-41 via a simple method. Application of this linked azacrown ether functionalized MCM-41 catalyst was also investigated as an effective, heterogeneous and host material in the regioselective ring opening and triazole cyclization of epoxides by phenylacetylene and sodium azide in click reaction. The heterogeneous catalyst was characterized by TGA,XRD,TEM, ¹HNMR, ¹³CNMR and FT-IR techniques. The results of theses anal. showed that, MCM-41@azacrown-Cu with a 22.99% mol loading of copper has given excellent catalytic activity and high efficiency in short time. It is noted that one of the most valuable factors in this work is the recyclability of the catalyst.

Journal of Porous Materials published new progress about 5411-14-3. 5411-14-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2,2-(1,2-Phenylenebis(oxy))diacetic acid, and the molecular formula is C10H10O3, HPLC of Formula: 5411-14-3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Shirali, Somayeh published the artcilePreparation and Characterization of Novel Hybrid Nanomaterial Catalyst MCM-41@AzaCrown-SB-cu and its Application in Synthesis of Hexahydroquinoline Derivatives under Solvent-Free Conditions, Safety of 2,2-(1,2-Phenylenebis(oxy))diacetic acid, the publication is Silicon (2021), 13(8), 2479-2491, database is CAplus.

Synthesis of efficient and reusable catalyst was carried out by immobilizing azacrown ether onto the covalently linked amine-functionalized mesoporous MCM-41 via a simple method. Application of this linked azacrown ether functionalized MCM-41 catalyst was also investigated as an effective, heterogeneous in the synthesis of hexahydroquinoline derivatives I (R = H, 4-Me, 4-Cl, etc.) under solvent-free conditions at environment temperature The heterogeneous catalyst is characterized by TGA, XRD, TEM, ¹HNMR, ¹³CNMR, and FT-IR techniques. The results of theses anal. showed that, MCM-41@azacrown-SB-Cu catalyst with a 22.99% mol loading of copper has given excellent catalytic activity and high efficiency in a short time. It is noted that one of the most valuable factors in this work is the recyclability of the catalyst.

Silicon published new progress about 5411-14-3. 5411-14-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2,2-(1,2-Phenylenebis(oxy))diacetic acid, and the molecular formula is C10H12F6N4O6PdS2, Safety of 2,2-(1,2-Phenylenebis(oxy))diacetic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Tymann, Dina Christina published the artcilePhotochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two-Carbon Ring-Expansion, Product Details of C10H15NS, the publication is Chemistry – A European Journal (2020), 26(52), 11974-11978, database is CAplus and MEDLINE.

The implementation of the concept of a photochem. elicited two-carbon homologation of a π-donor-π-acceptor substituted chromophore by triple-bond insertion was reported. Implementing a Ph connector between the slide-in module and the chromophore enabled the synthesis of cyclohepta[b]indole-type building blocks by a metal-free annulative one-pot two-carbon ring expansion of the five-membered chromophore. Post-irradiative structural elaboration provided founding members of the indolo[2,3-d]tropone family of compounds Control experiments in combination with computational chem. on this multibond reorganization process founded the basis for a mechanistic hypothesis.

Chemistry – A European Journal published new progress about 19117-31-8. 19117-31-8 belongs to catalysis-chemistry, auxiliary class Oxidant, name is N-(tert-Butyl)-S-phenylthiohydroxylamine, and the molecular formula is C15H14O3, Product Details of C10H15NS.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Schmid, H. published the artcileThe constitution of fulvoplumierin. II, Computed Properties of 3115-28-4, the publication is Helvetica Chimica Acta (1953), 1468-89, database is CAplus.

cf. C.A. 48, 1365a. Fulvoplumierin (I), hydrogenated in AcOEt over 5% Pd-CaCO₃ poisoned with Pb, absorbed 2.0 mol H to form 46% tetrahydrofulvoplumierin (II), C₁₄H₁₆O₄, yellow needles (from EtOH), m. 75-6° (reduces Tollens reagent, and gives a yellow color with EtONa in Me₂CO), and a little hexahydrofulvoplumierin (III). II in AcOEt was hydrogenated over Pd-CaCO₃ to 64% III. Ozonization of II in CHCl₃ gave BuCO₂H (p-toluidide, m. 69-71°, mixed m.p. 70-2°), also obtained by oxidation of II with KMnO₄. I, hydrogenated in AcOEt over Pd-CaCO₃, absorbed 2.9 mol H to give a mixture, separated by distillation and chromatog. into 1.5% II; 36% III, C₁₄H₁₈O₄, colorless needles (from MeOH-H₂O), m. 43.0-3.2°, b_0.02 120-30°, has 1 MeO group, no active H, slowly reduces Tollens reagent; 3.5% isohexahydrofulvoplumierin (IV), C₁₄H₁₈O₄, m. 74-4.5° (from MeOH-H₂O) (m.p. depressed by II), b_0.02 120°, has 1 MeO group, slowly reduces Tollens reagents; 8% octahydrofulvoplumierin (V), C₁₄H₂₀O₄, b_0.01 at 130°; and an oil, which was saponified to a monocarboxylic acid (VI), C₁₃H₁₈O₄, m. 91-2.5° (from C₆H₆-petr. ether), equivalent weight 246, λ_maximum 243 mμ (log ε 3.88) (in EtOH). III in AcOH, hydrogenated over PtO₂, absorbed 2.8 mol H and gave 15% decahydrofulvoplumierin (VII), C₁₄H₂₂O₄, m. 41.5-3.0°, and 68% of an acid (VIII), C₁₄H₂₄O₄. III did not react with MeNH₂.HCl in EtOH, or with Ac₂O, AcOH, and AcONH₄, or with CH₂N₂ in Et₂O. III, treated 20 h. with N NaOH at 125°, consumed 3 equivalents NaOH; acidification gave HCO₂H, identified as HCONHPh (m. and mixed m.p. 45.5-6.5°), and 88% of a dibasic acid (IX), C₁₂H₁₈O₄, m. 159-60° (from Et₂O or Me₂CO-H₂O), equivalent weight 115, pK₁ 4.25, pK₂ 7.00, having 1 C-Me (Kuhn-Roth oxidation), no MeO. Ozonolysis of III in EtCl at -14° gave HCO₂H (identified as HCONHPh), (CO₂H)₂, and 2-butylglutaric acid (X), C₉H₁₆O₄, m. 89-40.5°, mixed m.p. 39.5-41°, equivalent weight 99, pK₁ 4.16, pK₂ 5.24. X, m. 40-1° (from Et₂O-C₅H₁₂), was prepared in good yield by acid hydrolysis of BuC(CO₂Et)₂CHCH₂CO₂Et, b_0.23 128°, obtained in 72% yield by condensation of BuCH(CO₂Et)₂ and BrCH₂CH₂CO₂Et with Na in EtOH. IX was unaffected when heated 1 h. with 5% HCl at 180°. IX, hydrogenated over PtO₂ in AcOH, absorbed 1.0 mol H and gave an oily dibasic acid (XI), C₁₂H₂₀O₄, b_0.01 150°, equivalent weight 119, pK₁ 4.56, pK₂ 5.90. IX, heated 30 min. with Ac₂O at 155-60°, yielded a colorless add anhydride (XII), C₁₄H₁₈O₄, m. 70.5-1°, pK 2.52, equivalent weight 255, giving an intensive violet color with FeCl₃ and a pos. CHI₃ test, and forming stable salts which give back XII on acidification. Ozonolysis of IX in AcOEt at -14° gave 1.83 mol CO₂ and AcCH₂CH₂CHBuCO₂H (XIII), C₁₀H₁₈O₂, equivalent weight 195, having 2 C-Me group, and giving a pos. CHI₃ test; Clemmensen reduction of XIII gave Bu₂CHCO₂H (XIV), b₁₃, 150-70°, 2,4,6-tribromoanilide, m. and mixed m.p. 203.5-4.5° β-naphthylamide, m. and mixed m. 136-7.5°. For comparison with XIV, BuCHEt(CH₂)₂CO₂H (piperazine salt, m. 110°); [2,4,6-tribromoanilide, m. 96.5-7.0° (from EtOH)], was prepared by reduction of BuCHEtCO₂H with LiAlH₄ to BuCHEtCH₂OH, b₁₂ 79°, conversion to the bromide, condensation to BuCHEtCH₂CH(CO₂H)₂, m. 99.0-9.5°, and decarboxylation. The UV spectrum of IX showed it to be an α,β-unsaturated acid, and the formation of XII, X, and XIII established IX as being 3-butyl-2-carboxy-1-cyclopentene-1-acetic acid. 2-carboxy-1-cyclopentene-1-acetic acid (XV), C₈H₁₀O₄, m. 187°, equivalent weight 86, pK₁ 4.19, pK₂ 6.60, has an UV spectrum similar to that of IX, and was converted by boiling Ac₂O to an acid anhydride similar to XII, 3-hydroxy-4-acetyl-6,7-dihydrocyclopenta[c]pyran-1(5H)-one (XVI), C₁₀H₁₀H₄, m. 170-1°, colorless needles (from Me₂CO-H₂O), equivalent weight 203, pK 2.30, giving an intense violet color with FeCl₃. XII and XVI also have similar UV spectra in acids and in bases and show similar titration curves with NaOH, as do IX and XV. XII is therefore 3-hydroxy-4-acetyl-7-butyl-6,7-dihydrocyclopenta[c]pyran-1-(5H)-one, III is Me 7-butyl-6,7-dihydrocyclopenta[c]pyran-1(5H)-one-4-carboxylate, and XI is 3-butyl-2-carboxycyclopentane-1-acetic acid. IV, hydrogenated over PtO₂ in AcOH, absorbed 2.5 mol H and gave a mixture of VII and VIII. Ozonolysis of IV in CHCl₃ at -20° gave BuCO(CH₂)₂CO₂H (XVII), identified as its p-nitrophenylhydrazone, m. and mixed m. 149-50° (from EtOH-H₂O). XVII, m. 52-3° (from Et₂O-C₅H₁₂ or EtOH-H₂O), was prepared by saponification of its Et ester, b₁₃ 114°, obtained in 55% yield from EtO₂CCH₂CH₂COCl and Bu₂Cd in C₆H₆. From its UV spectrum (λ_maximum 285 mμ), IV has both double bonds conjugated with the carboxy group, and is therefore Me 7-butyl-5,6-dihydrocyclopenta[c]pyran-1(3H)-one-4-carboxylate. V, hydrogenated in AcOH over PtO₂, absorbed 1.0 mol H, and gave VII. Saponification of V yielded a small amount of a hydroxy dicarboxylic acid (XVIII), C₁₃H₂₀O₅, m. 132.5-3.0° (from Et₂O-petr. ether or Me₂CO-H₂O), equivalent weight 133, pK₁, 5.30, pK₂ 6.52, λ_maximum 232 mμ (log ε 4.02) (in EtOH), which does not lactonize easily. XVIII is probably 2-(2-carboxy-3-butyl-2cyclopenten-1-yl)-3-hydroxypropionic acid, and V is either Me 7-butyl-3,4,6,7-tetrahydrocyclopenta[c]pyran-1(5H)-one-4-carboxylate or Me 7 -butyl-4,4a,5,6-tetrahydrocyclopenta[c]pyran-1(3H)-one-4-carboxylate or a mixture of both forms. By analogy, and from its UV spectrum, VI is 7-butyl-3,4,6,7-tetrahydrocyclopenta[c] pyran-1(5H)-one-4-carboxylic acid or 7-butyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(3H)-one-4-carboxylic acid. I, hydrogenated completely in AcOH over PtO₂, gave VII and a mixture of other products which was saponified and then oxidized; KMnO₄ gave (CO₂H)₂, XVII, and a lactonic acid (XIX), C₁₃H₂₀O₄, m. 87.5-8.5°, equivalent weight 247; H₂CrO₄ gave BuCO₂H, PrCO₂H, and (CH₂CO₂H)₂. VII is Me 7-butylhexahydrocyclopenta[c]pyran-1(3H)-one-4-carboxylate, XIX is the corresponding free acid, and VIII is 2-(2-carboxy-3-butylcyclopentyl)propionic acid. The UV spectrum of II shows a double bond, conjugated with those in the pyrone ring, which must be in the cyclopentane ring, since oxidation of II gave BuCO₂H; II is probably Me 7-butylcyclopenta[c]pyran-1(5H)-one-4-carboxylate. From the structures of its derivatives, the similarity of its UV spectrum to those of 1-cinnamylideneindene and 1-crotonylideneindene (orange oil, C₁₃H₁₂, b_0.05 90°; picrate, orange needles, m. 90-90.5°) and the lack of allene group absorption bands in its IR spectrum, I must be a fulvene derivative, Me 7-crotonylidenecyclopenta[c]pyran-1(7H)-one-4-carboxylate.

Helvetica Chimica Acta published new progress about 3115-28-4. 3115-28-4 belongs to catalysis-chemistry, auxiliary class Aliphatic Chain, name is 2-Butylhexanoic acid, and the molecular formula is C10H20O2, Computed Properties of 3115-28-4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia