Month: December 2022

Baehr, Susanne published the artcileSelective Enzymatic Oxidation of Silanes to Silanols, Quality Control of 597-52-4, the publication is Angewandte Chemie, International Edition (2020), 59(36), 15507-15511, database is CAplus and MEDLINE.

Compared to the biol. world’s rich chem. for functionalizing carbon, enzymic transformations of the heavier homolog silicon are rare. We report that a wild-type cytochrome P 450 monooxygenase (P 450_BM3 from Bacillus megaterium, CYP102A1) has promiscuous activity for oxidation of hydrosilanes to give silanols. Directed evolution was applied to enhance this non-native activity and create a highly efficient catalyst for selective silane oxidation under mild conditions with oxygen as the terminal oxidant. The evolved enzyme leaves C-H bonds present in the silane substrates untouched, and this biotransformation does not lead to disiloxane formation, a common problem in silanol syntheses. Computational studies reveal that catalysis proceeds through hydrogen atom abstraction followed by radical rebound, as observed in the native C-H hydroxylation mechanism of the P 450 enzyme. This enzymic silane oxidation extends nature’s impressive catalytic repertoire.

Angewandte Chemie, International Edition published new progress about 597-52-4. 597-52-4 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is Triethylsilanol, and the molecular formula is C6H16OSi, Quality Control of 597-52-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Lewin, Anita H. published the artcileSynthesis and Characterization of the Selective, Reversible PKC_β Inhibitor (9S)-9-[(Dimethylamino)methyl]-6,7,10,11-tetrahydro-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione, Ruboxistaurin (LY333531), SDS of cas: 57044-25-4, the publication is ACS Chemical Neuroscience (2019), 10(1), 246-251, database is CAplus and MEDLINE.

The demonstrated role of PKC_β in mediating amphetamine-stimulated dopamine efflux, which regulates amphetamine-induced dopamine transporter trafficking and activity, has promoted the research use of the selective, reversible PKC_β inhibitor (9S)-9-[(dimethylamino)methyl]-6,7,10,11-tetrahydro-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione, ruboxistaurin. Despite the interest in development of ruboxistaurin as the mesylate monohydrate (Arxxant) for the treatment of diabetic retinopathy, macular edema, and nephropathy, several crucial details in physicochem. characterization were erroneous or missing. This report describes the synthesis and full characterization of ruboxistaurin free base (as a monohydrate), including X-ray crystallog. to confirm the absolute configuration, and of the mesylate salt, isolated as a hydrate containing 1.5 mol of water per mol.

ACS Chemical Neuroscience published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, SDS of cas: 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Molins-Molina, Oscar published the artcileSinglet oxygen production and in vitro phototoxicity studies on fenofibrate, mycophenolate mofetil, trifusal, and their active metabolites, Safety of 2-Hydroxy-4-(trifluoromethyl)benzoic acid, the publication is Journal of Physical Organic Chemistry (2017), 30(9), n/a, database is CAplus.

Singlet oxygen photosensitization (studied by time-resolved near-IR emission spectroscopy) and in vitro phototoxicity (by means of the 3T3 neutral red uptake assay) have been investigated for the prodrugs fenofibrate (FFB), mycophenolate mofetil (MMP), and trifusal (TFS) as well as for their active metabolites fenofibric acid (FFA), mycophenolic acid (MPA), and 2-hydroxy-4-(trifluoromethyl)benzoic acid (HTB). The results show that FFB and its active metabolite FFA generate ¹O₂ with a quantum yield in the range 0.30 to 0.40 and show a photo-irritation factor (PIF) higher than 40. By contrast, MMP/MPA and TFS/HTB are not photoactive in the used assays. These results correlate well with the previously reported in vivo phototoxicity in treated patients.

Journal of Physical Organic Chemistry published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Safety of 2-Hydroxy-4-(trifluoromethyl)benzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Furkert, Daniel P. published the artcileNonsymmetrical Azocarbonamide Carboxylates as Effective Mitsunobu Reagents, Related Products of alcohols-buliding-blocks, the publication is European Journal of Organic Chemistry (2014), 2014(35), 7806-7809, database is CAplus.

The nonsym. Mitsunobu reagents possessing both dialkyl amide and ester substituents was developed. These new reagents were readily prepared in a single pot from inexpensive, com. available materials by using a scalable and environmentally friendly procedure. They were shown to exhibit activity parallel to that of di-Et azodicarboxylate/diisopropyl azodicarboxylate in a wide variety of Mitsunobu reactions. Importantly, the acyl hydrazine reaction byproducts were readily separable from the crude mixture by standard aqueous workup. In addition, the discovery of effective nonsym. Mitsunobu reagents offers new directions for the ongoing development of this important reaction.

European Journal of Organic Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Strunskaya, E. I. published the artcileSynthesis of aryloxy-substituted 1,2,5-thiadiazoles by the Ullmann reaction, Formula: C6H9N3O2S, the publication is Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) (2001), 37(9), 1330-1334, database is CAplus.

3-Aryloxy-1,2,5-thiadiazoles were synthesized by the Ullmann reaction either from 3-chloro-1,2,5-thiadiazoles and phenols having donor substituents or from 3-hydroxy-1,2,5-thiadiazoles and chlorobenzenes containing acceptor substituents.

Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) published new progress about 30165-97-0. 30165-97-0 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Thiadiazole,Alcohol, name is 4-Morpholino-1,2,5-thiadiazol-3-ol, and the molecular formula is C10H14N2O, Formula: C6H9N3O2S.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Achour, Mariem published the artcileBioavailability and nutrikinetics of rosemary tea phenolic compounds in humans, HPLC of Formula: 621-37-4, the publication is Food Research International (2021), 109815, database is CAplus and MEDLINE.

Rosmarinus officinalis L. is a widespread aromatic plant commonly consumed as a tea in traditional cuisine and in folk medicine to treat various illnesses due to its therapeutic properties. To the best of our knowledge, there are no reports on the bioavailability and metabolism of R. officinalis tea polyphenols in humans. This study was aimed at assessing the bioavailability and nutrikinetics of R. officinalis phenolic compounds in healthy humans for the first time. Forty-eight compounds were identified in plasma and urine. Few un-metabolized compounds were detected since rosemary polyphenols were extensively metabolized into phase II conjugates, with rapid appearance and clearance in plasma, pointing to small intestinal absorption. Phase II derivatives of caffeic acid showed kinetics compatible with both intestinal and colonic hydrolysis of rosmarinic acid yielding free caffeic and 3,4-dihydroxyphenyl-lactic acids, which were absorbed and metabolized into phase II derivatives These metabolites, along with reduced forms of caffeic acid and their phase II metabolites, and those of hydroxyphenylpropionic, hydroxylphenylacetic, benzoic and hippuric acids, highlight the importance of colonic absorption. Total urinary excretion of the phenols added up to 235 μmol, corresponding to 22.3% of the ingested amount (1055 μM). In conclusion, rosemary tea polyphenols are partially bioavailable and extensively metabolized, mainly by the colonic microbiota.

Food Research International published new progress about 621-37-4. 621-37-4 belongs to alcohols-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Phenol,Natural product, name is 3-Hydroxyphenylacetic acid, and the molecular formula is C8H8O3, HPLC of Formula: 621-37-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Tomar, Pooja published the artcilePhotochemical activation of SF₆ by N-heterocyclic carbenes to provide a deoxyfluorinating reagent, Synthetic Route of 2240-88-2, the publication is Chemical Communications (Cambridge, United Kingdom) (2018), 54(70), 9753-9756, database is CAplus and MEDLINE.

The activation of the greenhouse gas SF₆ using electron-rich N-heterocyclic carbenes gave 2,2-difluoroimidazolines or 2,2-difluoroimidazolidines as well as 2-thio derivatives of the carbene precursors. The N-heterocyclic carbenes can also convert SF₄ to give similar products. The difluoroimidazolidine derivatives were applied in deoxyfluorination reactions. Furthermore, the activation of SF₆ and the fluorination can be coupled in a one-pot process to convert 1-octanol into 1-fluorooctane.

Chemical Communications (Cambridge, United Kingdom) published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C7H13BrSi, Synthetic Route of 2240-88-2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Salomon, Marcel Ahijado published the artcileStepwise oxygenation of pinacolborane by a rhodiumperoxo complex: detection of an intermediate metal borate and perborate, Quality Control of 25240-59-9, the publication is Angewandte Chemie, International Edition (2008), 47(46), 8867-8871, database is CAplus and MEDLINE.

Acting as go-between: A Rh borate and perborate were identified as intermediates in the Rh-mediated oxygenation of pinacolborane (HBpin). The Rh(III)-peroxo complex reacts with the Lewis acidic B compound HBpin by O transfer from the Rh center to HBpin to give a Rh(I) species. The reaction sequence might play a crucial role in the homocoupling of boronic acid.

Angewandte Chemie, International Edition published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Quality Control of 25240-59-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Colella, L. published the artcileOutside rules inside: the role of electron-active substituents in thiophene-based heterophenoquinones, Application of 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, the publication is Physical Chemistry Chemical Physics (2015), 17(16), 10426-10437, database is CAplus and MEDLINE.

The biradicaloid vs. quinoidal character of the ground state of thiophene-based heterophenoquinones bearing donor or acceptor groups is investigated. Keeping the conjugation length fixed, namely, the 5,5′-bis(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadiene-1-ylidene)-2,2′-dihydroxy bithiophene backbone, an opposite effect occurs depending on the donating or withdrawing nature of the substituents. The character of the ground state depends not only on the electronic nature of the substituents but also on their position on the mol. skeleton: donor groups on the 3,3′-positions of the bithiophene central core stabilize a quinoidal ground state, whereas a biradicaloid electronic structure results from the introduction of the same donor groups onto the lateral phenones. Withdrawing groups behave similar to donors, but in the opposite direction.

Physical Chemistry Chemical Physics published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C20H28B2O4S2, Application of 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Mowbray, Charles E. published the artcileDNDI-6148: A Novel Benzoxaborole Preclinical Candidate for the Treatment of Visceral Leishmaniasis, Application In Synthesis of 2240-88-2, the publication is Journal of Medicinal Chemistry (2021), 64(21), 16159-16176, database is CAplus and MEDLINE.

Visceral leishmaniasis (VL) is a parasitic disease endemic across multiple regions of the world and is fatal if untreated. Current therapies are unsuitable, and there is an urgent need for safe, short-course, and low-cost oral treatments to combat this neglected disease. The benzoxaborole chemotype has previously delivered clin. candidates for the treatment of other parasitic diseases. Here, we describe the development and optimization of this series, leading to the identification of compounds with potent in vitro and in vivo antileishmanial activity. The lead compound (DNDI-6148) combines impressive in vivo efficacy (>98% reduction in parasite burden) with pharmaceutical properties suitable for onward development and an acceptable safety profile. Detailed mode of action studies confirm that DNDI-6148 acts principally through the inhibition of Leishmania cleavage and polyadenylation specificity factor (CPSF3) endonuclease. As a result of these studies and its promising profile, DNDI-6148 has been declared a preclin. candidate for the treatment of VL.

Journal of Medicinal Chemistry published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Application In Synthesis of 2240-88-2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts