Tag: 100-200

In 2006,Cole, Andrew G.; Stroke, Ilana L.; Brescia, Marc-Raleigh; Simhadri, Srilatha; Zhang, Joan J.; Hussain, Zahid; Snider, Michael; Haskell, Christopher; Ribeiro, Sofia; Appell, Kenneth C.; Henderson, Ian; Webb, Maria L. published 《Identification and initial evaluation of 4-N-aryl-[1,4]diazepane ureas as potent CXCR3 antagonists》.Bioorganic & Medicinal Chemistry Letters published the findings.Formula: C8H6FNO4 The information in the text is summarized as follows:

The identification and evaluation of aryl-[1,4]diazepane ureas as functional antagonists of the chemokine receptor CXCR3 are described. Specific examples exhibit IC50 values of ∼60 nM in a calcium mobilization functional assay, and dose-dependently inhibit CXCR3 functional response to CXCL11 (interferon-inducible T-cell α chemoattractant/I-TAC) as measured by T-cell chemotaxis, with a potency of approx. 100 nM.Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9Formula: C8H6FNO4) was used in this study.

Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9) belongs to methyl benzoate. Methyl benzoate reacts at both the ring and the ester, depending on the substrate. Electrophiles attack the ring, illustrated by acid-catalysed nitration with nitric acid to give methyl 3-nitrobenzoate.Formula: C8H6FNO4Methyl 4-fluoro-3-nitrobenzoate is used to prepare dimethyl 3-nitro-3′,4-oxydibenzoate by reacting with 3-hydroxy-benzoic acid methyl ester.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In 2001,Lee, Chul Bom; Wu, Zhicai; Zhang, Fei; Chappell, Mark D.; Stachel, Shawn J.; Chou, Ting-Chao; Guan, Yongbiao; Danishefsky, Samuel J. published 《Insights into Long-Range Structural Effects on the Stereochemistry of Aldol Condensations: A Practical Total Synthesis of Desoxyepothilone F》.Journal of the American Chemical Society published the findings.Recommanded Product: 16982-21-1 The information in the text is summarized as follows:

A processable total synthesis of a potent antitumor agent, desoxyepothilone F [dEpoF, 21-hydroxy-12,13-desoxyepothilone B, 21-hydroxyepothilone D (I; R1 = Me, R2 = OH)], has been accomplished. The route is highly convergent. The new technol. has also been applied to a total synthesis of 12,13-desoxyepothilone B [dEpoB (I; R1 = Me, R2 = H)]. The crucial point of departure from previous syntheses of I (R1 = Me, R2 = H, OH) involves presentation of the C1-C11 sector for Suzuki coupling with C3 in reduced form. Hitherto, the required S stereochem. at C3 had been implemented via reduction of a keto function after Suzuki coupling. Whereas that chem. worked quite well in a synthesis of I (R1 = Me, R2 = H), it was not transferable to a high-yielding synthesis of I (R1 = Me, R2 = OH). The reduction of the keto group at C3 via a Noyori protocol after Suzuki coupling had proved to be very difficult. In our current approach, two consecutive aldol reactions are used to fashion the acyl sector. In the first aldol condensation, C6 becomes attached to C7. Following protection at C7, a two-carbon acetate equivalent is used to join C2 and C3 with very high asym. induction at C3. Only after this center has been implemented is the Suzuki reaction conducted. This major advance allowed us to synthesize I (R1 = Me, R2 = OH) in a straightforward fashion. These findings found ready application in the total synthesis of dEpoB. Another part of the study involved anal. of the factors associated with aldol condensations joining C6 to C7. In the work described herein, the consequences of the status of C3 in promoting the C6-C7 aldol coupling are probed in detail. Dramatic stereochem. long-range effects uncovered during the study are described, and a working model to explain these effects has emerged. In the experimental materials used by the author, we found Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1Recommanded Product: 16982-21-1)

Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1) belongs to anime. Reaction with nitrous acid (HNO2), which functions as an acylating agent that is a source of the nitrosyl group (―NO), converts aliphatic primary amines to nitrogen and mixtures of alkenes and alcohols corresponding to the alkyl group in a complex process. This reaction has been used for analytical determination of primary amino groups in a procedure known as the Van Slyke method.Recommanded Product: 16982-21-1

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In 2019,Catalysis Science & Technology included an article by Mourelle-Insua, Angela; Mendez-Sanchez, Daniel; Galman, James L.; Slabu, Iustina; Turner, Nicholas J.; Gotor-Fernandez, Vicente; Lavandera, Ivan. Product Details of 30414-53-0. The article was titled 《Efficient synthesis of α-alkyl-β-amino amides by transaminase-mediated dynamic kinetic resolutions》. The information in the text is summarized as follows:

The biocatalytic stereocontrolled synthesis of various acyclic anti- or syn-α-alkyl-β-amino amides through a dynamic kinetic resolution strategy is demonstrated. A series of com. available and inhouse transaminases (TAs) were employed to perform the transamination of a series of chem. synthesized racemic α-alkyl-β-keto amides. Among them, com. (R)-selective TAs showed the best activities and selectivities, giving access preferentially to the anti-diastereoisomers with low to high diastereomeric ratios (up to 96%) and excellent enantiomeric excess (>99%). The stereoselective biotransamination experiments were successfully demonstrated at a semi-preparative scale (25 mM, 100 mg substrate), leading to the corresponding optically active α-alkyl-β-amino amides in 45-90% isolated yields after a simple liquid-liquid extraction protocol. The experimental part of the paper was very detailed, including the reaction process of Methyl 3-oxovalerate(cas: 30414-53-0Product Details of 30414-53-0)

Methyl 3-oxovalerate(cas: 30414-53-0) belongs to ketone compounds. Ketone compounds have important physiological properties. They are found in several sugars and in compounds for medicinal use, including natural and synthetic steroid hormones. Molecules of the anti-inflammatory agent cortisone contain three ketone groups.Product Details of 30414-53-0

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In 2019,Advanced Synthesis & Catalysis included an article by Mendez-Sanchez, Daniel; Mourelle-Insua, Angela; Gotor-Fernandez, Vicente; Lavandera, Ivan. Category: esters-buliding-blocks. The article was titled 《Synthesis of α-Alkyl-β-Hydroxy Amides through Biocatalytic Dynamic Kinetic Resolution Employing Alcohol Dehydrogenases》. The information in the text is summarized as follows:

Chiral (α-substituted) β-hydroxy amides are interesting derivatives as they are useful building blocks of many biol. active compounds Herein, the biocatalytic stereocontrolled synthesis of various acyclic syn-α-alkyl-β-hydroxy amides through a dynamic kinetic resolution is shown. Hence, a series of overexpressed alc. dehydrogenases (ADHs) in Escherichia coli was used to reduce the corresponding racemic β-keto amides. Among them, ADH-A from Rhodococcus ruber and com. evo-1.1.200 afforded the best activities and selectivities, giving access to the opposite enantiomers with high diastereomeric excess and excellent enantiomeric excess. Some of these compounds were obtained at semipreparative scale. In the part of experimental materials, we found many familiar compounds, such as Methyl 3-oxovalerate(cas: 30414-53-0Category: esters-buliding-blocks)

Methyl 3-oxovalerate(cas: 30414-53-0) belongs to ketone compounds. Ketone compounds have important physiological properties. They are found in several sugars and in compounds for medicinal use, including natural and synthetic steroid hormones. Molecules of the anti-inflammatory agent cortisone contain three ketone groups.Category: esters-buliding-blocks

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

《Structure-Based Design of Tricyclic NF-κB Inducing Kinase (NIK) Inhibitors That Have High Selectivity over Phosphoinositide-3-kinase (PI3K)》 was written by Castanedo, Georgette M.; Blaquiere, Nicole; Beresini, Maureen; Bravo, Brandon; Brightbill, Hans; Chen, Jacob; Cui, Hai-Feng; Eigenbrot, Charles; Everett, Christine; Feng, Jianwen; Godemann, Robert; Gogol, Emily; Hymowitz, Sarah; Johnson, Adam; Kayagaki, Nobuhiko; Kohli, Pawan Bir; Knuppel, Kathleen; Kraemer, Joachim; Kruger, Susan; Loke, Pui; McEwan, Paul; Montalbetti, Christian; Roberts, David A.; Smith, Myron; Steinbacher, Stefan; Sujatha-Bhaskar, Swathi; Takahashi, Ryan; Wang, Xiaolu; Wu, Lawren C.; Zhang, Yamin; Staben, Steven T.. Product Details of 16982-21-1This research focused ontricyclic benzoxepin preparation NFkappaB inducing kinase inhibitor phosphoinositidekinase PI3K. The article conveys some information:

The authors report a structure-guided optimization of a novel series of NF-κB inducing kinase (NIK) inhibitors. Starting from a modestly potent, low mol. weight lead, activity was improved by designing a type I1/2 binding mode that accessed a back pocket past the methionine-471 gatekeeper. Divergent binding modes in NIK and PI3K were used to dampen PI3K-inhibition while maintaining NIK inhibition within these series. Potent compounds were discovered that selectively inhibit the nuclear translocation of NF-kB2 (p52/REL-B) but not canonical NF-kB1 (REL-A/p50). The results came from multiple reactions, including the reaction of Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1Product Details of 16982-21-1)

Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Product Details of 16982-21-1

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

《Photochemistry of two β,β’-epoxy ketones, 3-oxatricyclo[3.2.1.02,4]octan-8-one and 3-oxatricyclo[3.3.1.02.4]nonan-9-one. Intramolecular reactions of α,β-unsaturated aldehydo ketenes》 was published in Journal of Organic Chemistry in 1978. These research results belong to Ayral-Kaloustian, Semiramis; Wolff, Steven; Agosta, William C.. COA of Formula: C8H14O3 The article mentions the following:

Photolysis of epoxy ketone I in C6H6 leads to OHCCH:CHCH2CH2CH:CO (II) and β-lactone III as primary products. Subsequent addition of MeOH furnishes IV and V. Secondary photolysis of II yields the cycloaddition product VI. Photolysis of I in C6H6 containing 3% MeOH gives IV directly, along with VII. Similar irradiation of epoxy ketone VIII leads to OHCCH:CH(CH2)3CH:CO, which reacts with MeOH to give the aldehydo esters IX and X. The results came from multiple reactions, including the reaction of Cis-methyl 2-hydroxycyclohexanecarboxylate(cas: 936-03-8COA of Formula: C8H14O3)

Cis-methyl 2-hydroxycyclohexanecarboxylate(cas: 936-03-8) belongs to esters. They are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils.Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones.COA of Formula: C8H14O3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

《Deoxygenative Deuteration of Carboxylic Acids with D2O》 was published in Angewandte Chemie, International Edition in 2019. These research results belong to Zhang, Muliang; Yuan, Xiang-Ai; Zhu, Chengjian; Xie, Jin. HPLC of Formula: 1877-71-0 The article mentions the following:

C1-Deuterated aryl and alkyl aldehydes such as 4-PhC6H4CDO and PhCH2CH2CDO were prepared chemoselectively with 58-96% deuterium incorporation by reduction of aromatic and aliphatic carboxylic acids using iridium photocatalysts, either Ph3P or Ph2OEt as an oxygen acceptor, 2,4,6-i-Pr3C6H2SH as a hydrogen atom donor, and using D2O as an inexpensive deuterium source. The method was used for the preparation of deuterated derivatives of pharmaceuticals and natural products containing aromatic carboxylic acid moieties. The method was also used for chemoselective reduction of aryl and alkyl carboxylic acids to the corresponding aldehydes using H2O as a hydrogen atom source. In the experiment, the researchers used many compounds, for example, 3-(Methoxycarbonyl)benzoic acid(cas: 1877-71-0HPLC of Formula: 1877-71-0)

3-(Methoxycarbonyl)benzoic acid(cas: 1877-71-0) belongs to esters. Esters are more polar than ethers but less polar than alcohols. HPLC of Formula: 1877-71-0 They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

《Combined Theoretical and Experimental Studies Unravel Multiple Pathways to Convergent Asymmetric Hydrogenation of Enamides》 was written by Yang, Jianping; Massaro, Luca; Krajangsri, Suppachai; Singh, Thishana; Su, Hao; Silvi, Emanuele; Ponra, Sudipta; Eriksson, Lars; Ahlquist, Maarten S. G.; Andersson, Pher G.. Recommanded Product: 4755-77-5This research focused onvinyl oxazolidinone iridium catalyst enantioselective asym hydrogenation reaction; ethyl oxazolidinone preparation. The article conveys some information:

A highly efficient convergent asym. hydrogenation of E/Z mixtures of enamides catalyzed by N,P-iridium complexes supported by mechanistic studies was reported. It was found that reduction of the olefinic isomers (E and Z geometries) produced chiral amides with the same absolute configuration (enantioconvergent hydrogenation). This allowed the hydrogenation of a wide range of E/Z mixtures of trisubstituted enamides with excellent enantioselectivity (up to 99% ee). A detailed mechanistic study using deuterium labeling and kinetic experiments revealed two different pathways for the observed enantioconvergence. For α-aryl enamides, fast isomerization of the double bond took place, and the overall process resulted in kinetic resolution of the two isomers. For α-alkyl enamides, no double bond isomerization was detected, and competition experiments suggested that substrate chelation was responsible for the enantioconvergent stereochem. outcome. DFT calculations were performed to predict the correct absolute configuration of the products and strengthen the proposed mechanism of the iridium-catalyzed isomerization pathway. After reading the article, we found that the author used Ethyl oxalyl monochloride(cas: 4755-77-5Recommanded Product: 4755-77-5)

Ethyl oxalyl monochloride(cas: 4755-77-5) belongs to acyl chlorides. Lacking the ability to form hydrogen bonds, acyl chlorides have lower boiling and melting points than similar carboxylic acids. For example, acetic acid boils at 118 °C, whereas acetyl chloride boils at 51 °C. Like most carbonyl compounds, infrared spectroscopy reveals a band near 1750 cm−1.Recommanded Product: 4755-77-5

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

《Catalytic Cleavage of C(sp2)-C(sp2) Bonds with Rh-Carbynoids》 was written by Wang, Zhaofeng; Jiang, Liyin; Sarro, Pau; Suero, Marcos G.. Application In Synthesis of tert-Butyl carbamateThis research focused onunsaturated ester preparation; alkene diazoester hypervalent iodine cyclopropanation ring opening rhodium catalyst. The article conveys some information:

We report a catalytic strategy that generates rhodium-carbynoids by selective diazo activation of designed carbyne sources. We found that rhodium-carbynoid species provoke C(sp2)-C(sp2) bond scission in alkenes by inserting a monovalent carbon unit between both sp2-hybridized carbons. This skeletal remodeling process accesses synthetically useful allyl cation intermediates that conduct to valuable allylic building blocks upon nucleophile attack. Our results rely on the formation of cyclopropyl-I(III) intermediates able to undergo electrocyclic ring-opening, following the Woodward-Hoffmann-DePuy rules.tert-Butyl carbamate(cas: 4248-19-5Application In Synthesis of tert-Butyl carbamate) was used in this study.

tert-Butyl carbamate(cas: 4248-19-5) belongs to anime. Reaction with nitrous acid (HNO2), which functions as an acylating agent that is a source of the nitrosyl group (―NO), converts aliphatic primary amines to nitrogen and mixtures of alkenes and alcohols corresponding to the alkyl group in a complex process. This reaction has been used for analytical determination of primary amino groups in a procedure known as the Van Slyke method.Application In Synthesis of tert-Butyl carbamate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Formula: C4H7NO2SIn 2016 ,《Synthesis and biological evaluation of picolinamides and thiazole-2-carboxamides as mGluR5 (metabotropic glutamate receptor 5) antagonists》 was published in Bioorganic & Medicinal Chemistry Letters. The article was written by Vu, Hoang Nam; Kim, Ji Young; Hassan, Ahmed H. E.; Choi, Kihang; Park, Jong-Hyun; Park, Ki Duk; Lee, Jae Kyun; Pae, Ae Nim; Choo, Hyunah; Min, Sun-Joon; Cho, Yong Seo. The article contains the following contents:

Herein the synthesis and biol. evaluation of picolinamides and thiazole-2-carboxamides as potential mGluR5 antagonists are described. It was found that a series of N-aryl-4-R-2-thiazolecarboxamides (R = Br, Me, CN; aryl = 3-FC6H4, 3-NCC6H4, 2-pyridyl, 6-chloro-2-pyridyl, etc.) (I) showed better inhibitory activity against mGluR5. The compounds I (R = Br; aryl = 3-BrC6H4, 6-methyl-2-pyridyl) have been identified as potent antagonists (IC50 = 274 and 159 nM) showing excellent in vitro stability profile. Mol. docking study using the crystal structure of mGluR5 revealed that these two compounds fit the allosteric binding site of mavoglurant well. The experimental process involved the reaction of Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1Formula: C4H7NO2S)

Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.Formula: C4H7NO2S

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics