Tag: M.W=150-200

Cui, Lei published the artcileOnline application-oriented optimal scheduling for 2-keto-l-gulonic acid production, Recommanded Product: (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid, the publication is Canadian Journal of Chemical Engineering (2015), 93(7), 1160-1167, database is CAplus.

An optimal scheduling approach for the 2-keto-L-gulonic acid (2-KGA) fermentation process is proposed to improve allocation of L-sorbose resources with the aim of profit maximization in a multi-bioreactor workshop. The empirical operation in 2-KGA cultivation under study is to assign the same quantity of L-sorbose to each batch without taking batch-to-batch variations into account, while the optimal scheduling approach presented in this paper will determine L-sorbose feeding according to the evaluation of the profit-making ability of the individual batch. Each 2-KGA batch is classified online according to the prediction of the profit function, so that each batch is assigned into different profit-making categories. Pseudo-online scheduling is implemented with the data of industrial 2-KGA cultivations. A total profit increase of 6-7 % is found to be achievable for the workshop in comparison with the empirical operation.

Canadian Journal of Chemical Engineering published new progress about 526-98-7. 526-98-7 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Other Sugar Units, name is (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid, and the molecular formula is C6H10O7, Recommanded Product: (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid.

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

He, Huan published the artcileConcise total synthesis of opioids, Product Details of C9H11NO4, the publication is Organic Chemistry Frontiers (2022), 9(9), 2322-2327, database is CAplus.

Morphine and its related alkaloids are among the most representative natural medicines that have benefited human beings for over two centuries. Industrial manufacturing of these therapeutically valuable and structurally fascinating mols. relies on farming of opium poppies, causing severe soil erosion and regulation issues. Despite the advances in the development of numerous biosynthesis and chem. synthesis methods, a truly efficient approach to opioids which is competitive in terms of cost with the current manufacturing protocol remains highly desirable. Here we present a concise total synthesis of opioids exemplified by (-)-codeine, (-)-oxycodone, (-)-naloxone, and (-)-naltrexone with by far the highest overall yields (16-34%) from readily available starting materials. Remarkably, central to the success of the present synthesis is the development of a Pd-catalyzed dearomatization arene coupling reaction using an inexpensive, air stable, and robust phosphonium ligand. This bio-inspired step constructs the tetracyclic morphinan core in a manner with excellent regioselectivity, efficiency, and scalability.

Organic Chemistry Frontiers published new progress about 528594-30-1. 528594-30-1 belongs to alcohols-buliding-blocks, auxiliary class Nitro Compound,Benzene,Phenol,Ether, name is 2-Methoxy-4-(2-nitroethyl)phenol, and the molecular formula is C9H11NO4, Product Details of C9H11NO4.

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

Ghoshal, Anirban published the artcile[3 + 2]-Dipolar Cycloaddition of Aldehyde-Tethered Alkynamides and Trimethylsilyl Amino Esters: A Gateway to Uniquely Functionalized Polycyclic N-Heterocycles via Post-Ugi Functionalization, COA of Formula: C8H19NO2, the publication is Journal of Organic Chemistry (2020), 85(23), 14890-14904, database is CAplus and MEDLINE.

An efficient method for the generation of uniquely functionalized pyrrolo-pyrrolizinones, pyrido-pyrrolizinones, and azepino-pyrrolizinones via [3 + 2]-dipolar cycloaddition is described. The method involves the synthesis of tethered alkynamides using Ugi condensation and oxidation that were subsequently subjected to a dipolar cycloaddition reaction with trimethylsilyl amino esters. Further transformations to demonstrate the utility of these scaffolds were also investigated.

Journal of Organic Chemistry published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C8H19NO2, COA of Formula: C8H19NO2.

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

Baker, Sarah I. published the artcileEnhanced Reactivity for Aromatic Bromination via Halogen Bonding with Lactic Acid Derivatives, Safety of 2-Hydroxy-2-phenylacetic acid, the publication is Journal of Organic Chemistry (2022), 87(13), 8492-8502, database is CAplus and MEDLINE.

Herein, a new method for regioselective aromatic bromination using lactic acid derivatives as halogen bond acceptors with N-bromosuccinimide (NBS) is reported. Several structural analogs of lactic acid affected the efficiency of aromatic brominations, presumably via Lewis acid/base halogen-bonding interactions. Rate comparisons of aromatic brominations demonstrated the reactivity enhancement available via catalytic additives capable of halogen bonding. Computational results demonstrated that Lewis basic additives interact with NBS to increase the electropos. character of bromine prior to electrophilic transfer. An optimized procedure using catalytic mandelic acid under aqueous conditions at room temperature has been developed to promote aromatic bromination on a variety of arene substrates with complete regioselectivity.

Journal of Organic Chemistry published new progress about 90-64-2. 90-64-2 belongs to alcohols-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Alcohol,Natural product, name is 2-Hydroxy-2-phenylacetic acid, and the molecular formula is C8H8O3, Safety of 2-Hydroxy-2-phenylacetic acid.

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

Smolobochkin, Andrey V. published the artcileSynthesis of novel macrocyclic and heterocyclic taurine derivatives based on the reaction of sodium 2-[(4,4-diethoxybutyl)amino]ethanesulfonate with phenols, Application of 4,4-Diethoxybutan-1-amine, the publication is Chemistry of Heterocyclic Compounds (New York, NY, United States) (2020), 56(7), 888-891, database is CAplus.

An approach to the synthesis of novel macrocyclic and heterocyclic taurine derivatives I and II (R = H, Me, OH) based on the reaction of sodium 2-[(4,4-diethoxybutyl)amino]ethanesulfonate with phenols 2-R-3-OHC₆H₃OH in the presence of trifluoroacetic acid has been developed.

Chemistry of Heterocyclic Compounds (New York, NY, United States) published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C14H12N2S, Application of 4,4-Diethoxybutan-1-amine.

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

Wang, Yinli published the artcileEnhanced Molecular Recognition through Substrate-Additive Complex Formation in N-Heterocyclic-Carbene-Catalyzed Kinetic Resolution of α-Hydroxythioamides, COA of Formula: C8H8O3, the publication is ACS Catalysis (2022), 12(10), 6100-6107, database is CAplus.

A new way of understanding enhanced mol. recognition through substrate-additive complex formation and the development of the first catalytic kinetic resolution of α-hydroxythioamides RCH(OH)C(S)NH(R¹) (R = Me, cyclopropyl, Ph, etc.; R¹ = Et, t-Bu, 3,5-bis(trifluoromethyl)phenyl, etc.), which are versatile synthetic building blocks, using chiral N-heterocyclic carbene I-catalyzed enantioselective acylation assisted by a carboxylate additive viz., 9-Julolidinecarboxylic acid was described. Mass spectrometry provided evidence for the role of the additive, which forms a hydrogen-bonded complex with α-hydroxythioamide, resulting in both rate and selectivity enhancements. The synthetic applications of the resolved α-hydroxythioamides highlight the usefulness of the developed method.

ACS Catalysis published new progress about 90-64-2. 90-64-2 belongs to alcohols-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Alcohol,Natural product, name is 2-Hydroxy-2-phenylacetic acid, and the molecular formula is C7H9NO, COA of Formula: C8H8O3.

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

Hou, Wei published the artcileCloning, expression and activity analysis of sndh-sdh gene cluster of Gluconobacter oxydans, Category: alcohols-buliding-blocks, the publication is Shengwu Jishu Tongxun (2012), 23(3), 389-392, database is CAplus.

Objective: To clone the sndh-sdh gene cluster from Gluconobacter oxydans H763 and investigate the expression and biol. activity of sorbosone dehydrogenase-sorbose dehydrogenase (SNDH-SDH) in Escherichia coli DH5α and G. oxydans 621H. Methods & Results: The sndh-sdh gene cluster, including promoter, structural gene and terminator sequence, was directly amplified using PCR method from G. oxydans H763 genome DNA. Then the 3533 bp amplification product was retrieved and ligated into the vector pMD18T and transformed into E. coli DH5α. Its expression and biol. activity were examined by DCIP assay when sorbose or xylose was used as substrate. After the cell lysis was added to the DCIP detection solution, its color changed from bluish green to yellow, which suggested that the expression product had dehydrogenase activity. The vector pBBR1MCS2-sndh-sdh was constructed and conjugated into G. oxydans 621H. After the recombinant strain was cultivated in the medium containing sorbitol or sorbose as substrate, the metabolic products in the supernatant were assayed by thin-layer chromatog., and chromatoplate showed the 2-keto-L-gulonic acid (2-KLG) spots. Conclusion: The above results indicated that the SNDH-SDH was expressed in E. coli DH5α and G. oxydans 621H.

Shengwu Jishu Tongxun published new progress about 526-98-7. 526-98-7 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Other Sugar Units, name is (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid, and the molecular formula is C6H10O7, Category: alcohols-buliding-blocks.

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

Liu, Xiaojie published the artcileNi-Catalyzed Deoxygenative Borylation of Phenols Via O-Phenyl-uronium Activation, Formula: C10H9NO, the publication is ACS Catalysis (2022), 12(15), 8904-8910, database is CAplus.

Herein, we report an efficient method for the Ni-catalyzed deoxygenative borylation of unprotected phenols and also demonstrate that this Ni-catalyzed phenolic C(sp²)-O transformation is applicable to the Suzuki-Miyaura-type and Heck-type cross-couplings of phenols. Investigations on the reaction intermediate have revealed that the achievement of general, mild deoxygenative cross-coupling reactions of phenols is ascribed to the conversion of phenols into the unusual O-phenyl-uroniums that feature active phenolic C(sp²)-O bonds. The Ni-complex intermediate resulting from an oxidative addition of a phenolic C(sp²)-O bond to monophosphine-supported Ni(0) catalyst was characterized and confirmed to be (PCy₃)₂Ni(Ar)(F) complex, offering exptl. evidence for the generally proposed C(sp²)-O oxidative addition step.

ACS Catalysis published new progress about 23351-09-9. 23351-09-9 belongs to alcohols-buliding-blocks, auxiliary class Pyrrole,Benzene,Alcohol, name is 4-(1H-Pyrrol-1-yl)phenol, and the molecular formula is C10H9NO, Formula: C10H9NO.

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

Jaskiw, George E. published the artcileSmall phenolic and indolic gut-dependent molecules in the primate central nervous system: levels vs. bioactivity, Category: alcohols-buliding-blocks, the publication is Metabolomics (2022), 18(1), 8, database is CAplus and MEDLINE.

Rapidly growing body of data documents associations between disease of the brain and small mols. generated by gut-microbiota (GMB). While such metabolites can affect brain function through a variety of mechanisms, the most direct action would be on the central nervous system (CNS) itself. Identify indolic and phenolic GMB-dependent small mols. that reach bioactive concentrations in primate CNS. We conducted a PubMed search for metabolomic studies of the primate CNS [brain tissue or cerebrospinal fluid (CSF)] and then selected for phenolic or indolic metabolites that (i) had been quantified, (ii) were GMB-dependent. For each chem. we then conducted a search for studies of bioactivity conducted in vitro in human cells of any kind or in CNS cells from the mouse or rat. 36 metabolites of interests were identified in primate CNS through targeted metabolomics. Quantification was available for 31/36 and in vitro bioactivity for 23/36. The reported CNS range for 8 metabolites 2-(3-hydroxyphenyl)acetic acid, 2-(4-hydroxyphenyl)acetic acid, 3-(3-hydroxyphenyl)propanoic acid, (E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid [caffeic acid], 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 2-acetamido-3-(1H-indol-3-yl)propanoic acid [N-acetyltryptophan], 1H-indol-3-yl hydrogen sulfate [indoxyl-3-sulfate] overlapped with a bioactive concentration However, the number and quality of relevant studies of CNS neurochem. as well as of bioactivity were highly limited. Structural isomers, multiple metabolites and potential confounders were inadequately considered. The potential direct bioactivity of GMB-derived indolic and phenolic mols. on primate CNS remains largely unknown. The field requires addnl. strategies to identify and prioritize screening of the most promising small mols. that enter the CNS.

Metabolomics 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, Category: alcohols-buliding-blocks.

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

Shamim, Khalida published the artcileApplication of niclosamide and analogs as small molecule inhibitors of Zika virus and SARS-CoV-2 infection, Quality Control of 86-48-6, the publication is Bioorganic & Medicinal Chemistry Letters (2021), 127906, database is CAplus and MEDLINE.

Zika virus has emerged as a potential threat to human health globally. A previous drug repurposing screen identified the approved anthelminthic drug niclosamide as a small mol. inhibitor of Zika virus infection. However, as antihelminthic drugs are generally designed to have low absorption when dosed orally, the very limited bioavailability of niclosamide will likely hinder its potential direct repurposing as an antiviral medication. Here, we conducted SAR studies focusing on the anilide and salicylic acid regions of niclosamide to improve physicochem. properties such as microsomal metabolic stability, permeability and solubility We found that the 5-bromo substitution in the salicylic acid region retains potency while providing better drug-like properties. Other modifications in the anilide region with 2′-OMe and 2′-H substitutions were also advantageous. We found that the 4′-NO₂ substituent can be replaced with a 4′-CN or 4′-CF₃ substituents. Together, these modifications provide a basis for optimizing the structure of niclosamide to improve systemic exposure for application of niclosamide analogs as drug lead candidates for treating Zika and other viral infections. Indeed, key analogs were also able to rescue cells from the cytopathic effect of SARS-CoV-2 infection, indicating relevance for therapeutic strategies targeting the COVID-19 pandemic.

Bioorganic & Medicinal Chemistry Letters published new progress about 86-48-6. 86-48-6 belongs to alcohols-buliding-blocks, auxiliary class Organic Pigment,Natural product, name is 1-Hydroxy-2-naphthoic acid, and the molecular formula is C10H11ClO2S, Quality Control of 86-48-6.

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