Month: October 2022

Hirsh, Andrew J.; Molino, Bruce F.; Zhang, Jianzhong; Astakhova, Nadezhda; Geiss, William B.; Sargent, Bruce J.; Swenson, Brian D.; Usyatinsky, Alexander; Wyle, Michael J.; Boucher, Richard C.; Smith, Rick T.; Zamurs, Andra; Johnson, M. Ross published the artcile< Design, Synthesis, and Structure-Activity Relationships of Novel 2-Substituted Pyrazinoylguanidine Epithelial Sodium Channel Blockers: Drugs for Cystic Fibrosis and Chronic Bronchitis>, Application In Synthesis of 52244-70-9, the main research area is pyrazinoylguanidine epithelial sodium channel blocker preparation.

Amiloride, the prototypical epithelial sodium channel (ENaC) blocker, has been administered with limited success as aerosol therapy for improving pulmonary function in patients with the genetic disorder cystic fibrosis. This study was conducted to synthesize and identify more potent, less reversible ENaC blockers, targeted for aerosol therapy and possessing minimal systemic renal activity. A series of novel 2-substituted acylguanidine analogs of amiloride were synthesized and evaluated for potency and reversibility on bronchial ENaC. All compounds tested were more potent and less reversible at blocking sodium-dependent short-circuit current than amiloride. Compounds I [R = NH(CH2)4C6H4O(CH2)2OH-4, NH(CH2)4C6H4O(CH2)3OH-4, NH(CH2)4C6H4OCH2CH(OH)CH2OH-4 (both R and S isomers)] showed the greatest potency on ENaC with IC50 values below 10 nM. A regioselective difference in potency was found, whereas no stereospecific difference in potency on ENaC was displayed. Lead compound I [R = NH(CH2)4C6H4OCH2CH(OH)CH2OH-4 (racemic)] was 102-fold more potent and 5-fold less reversible than amiloride and displayed the lowest IC50 value ever reported for an ENaC blocker.

Journal of Medicinal Chemistry published new progress about Chronic bronchitis. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Application In Synthesis of 52244-70-9.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Bhole, Ritesh P.; Naksakhare, Sachin R.; Bonde, Chandrakant G. published the artcile< A stability indicating HPTLC Method for apremilast and identification of degradation products using MS/MS>, Electric Literature of 608141-42-0, the main research area is apremilast degradation product high performance liquid chromatog pharmaceutical formulation.

Aim: Apremilast is used for treatment of certain types of psoriasis, psoriatic arthritisand plaque psoriasis is a type of skin condition. An extensive literature search revealed that there exist very few methods on RP-HPLC reported and HPTLC method was not reported. This study deals with simple, precise, accurate and economical stability indicating HPTLC method development with validation as per ICH guidelines with application of developed method on in Apremilast pharmaceutical formulations and Identified and Characterization of degradation products using MS/MS. Method: Precoated Silica gels plates were used as stationary phase. Toluene: Et Acetate (4:6; volume/volume) was delivered best separation at 236 nm (Rf 0.55 ± 0.02) by densitometry anal. Degradation anal. was performed as per ICH guidelines (Q2R1). Isolation of degradation product by HPTLC method and identify by MS/MS method. Results: The linearity was 100-600 ng with R2 of 0.997 while, % RSD was in range. LOD and LOQ of Apremilast were found 0.77ng/spot and 2.35ng/spot resp. The recovery of Apremilast was found to be 99.70 ± 0.23%. The % assay of active substance was found in a range 80.62 to 100. HPTLC and MS/MS method revealed possible degradation mechanism of 11 degradant products. Conclusion: The Proposed developed and validated HPTLC method was found to be more sensitive, simple, precise, accurate, cost effective and robust. This method could be applied for anal. of bulk drug and tablet formulation, degradation study. This degradation pathway of drug will help to identify the degradation products of Apremilast.

Journal of Pharmaceutical Sciences and Research published new progress about HPLC. 608141-42-0 belongs to class ethers-buliding-blocks, and the molecular formula is C12H19NO4S, Electric Literature of 608141-42-0.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Wang, Tao; Hoffmann, Marvin; Dreuw, Andreas; Hasagic, Edina; Hu, Chao; Stein, Philipp M.; Witzel, Sina; Shi, Hongwei; Yang, Yangyang; Rudolph, Matthias; Stuck, Fabian; Rominger, Frank; Kerscher, Marion; Comba, Peter; Hashmi, A. Stephen K. published the artcile< A Metal-Free Direct Arene C-H Amination>, Recommanded Product: 2-Methoxy-N-methylaniline, the main research area is aryl amine preparation chemoselective; arene hydroxylamine amination.

Here, a metal-free arene e.g., mesitylene C-H amination using hydroxylamine derivatives 4-(CH3)C6H5S(O)2ON(R)R1 (R = H, Me; R1 = Me, Boc, Bn, etc.) under benign conditions was reported. A charge transfer interaction between the aminating reagents and the arene substrates enables the chemoselective amination of the arene, even in the presence of various functional groups. Oxygen was crucial for an effective conversion and its accelerating role for the electron transfer step was proven exptl. In addition, this was rationalized by a theor. study which indicated the involvement of a dioxygen-bridged complex with a “”Sandwich-like”” arrangement of the aromatic starting materials and the aminating agents at the dioxygen mol.

Advanced Synthesis & Catalysis published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 10541-78-3 belongs to class ethers-buliding-blocks, and the molecular formula is C8H11NO, Recommanded Product: 2-Methoxy-N-methylaniline.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Flippin, Lee A.; Muchowski, Joseph M.; Carter, David S. published the artcile< Directed metalation of aromatic aldimines with lithium 2,2,6,6-tetramethylpiperidide>, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde, the main research area is lithiation aromatic aldimine lithium tetramethylpiperidide; piperidide lithiotetramethyl lithiation aldimine; benzaldehyde methyl.

N-Cyclohexyl aromatic aldimines are ortho-lithiated or o-methyl-lithiated with 2 equiv of lithium 2,2,6,6-tetramethylpiperidide (LTMP) in THF solution at -15°. The lithiated intermediates generally reacted with alkyl halides or CO2 to provide ortho-functionalized aldimine products which could be readily converted to the corresponding aldehydes by hydrolysis with aqueous 4 M HCl. Aromatic aldimines derived from (±)-trans-2-methylcyclohexylamine or 3-amino-2,4-dimethylpentane are resistant toward C=N addition with 1 equiv of n-BuLi at 0° in THF solution; however, they are also surprisingly resistant toward directed metalation reactions with either LTMP or n-BuLi. Exceptions to the ortho-directing and o-methyl-directing effects of the aldimine group were observed in a reaction of 3-methylthiophene-2-carboxaldehyde cyclohexylimine with LTMP, followed by CH3I, which gave a 9:1 mixture of 3,5-dimethylthiophene-2-carboxaldehyde cyclohexylimine and 5-ethyl-3-methylthiophene-2-carboxaldehyde cyclohexylimine, and a reaction of p-tolualdehyde 2,4-dimethylpent-3-ylimine with either n-BuLi or LTMP, followed by CH3I, which gave p-ethylbenzaldehyde 2,4-dimethylpent-3-ylimine.

Journal of Organic Chemistry published new progress about Aldimines Role: RCT (Reactant), RACT (Reactant or Reagent). 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Wedler, C.; Haage, K.; Herbst, M.; Tischer, H.; Knofe, E. published the artcile< Preparation and some properties of amine oxides derived from defined ethylene oxide adducts>, Recommanded Product: 2,2′-(Tridecylazanediyl)diethanol, the main research area is amine oxide preparation solubility; bishydroxyethylalkylamine oxide preparation solubility; thermal analysis bishydroxyethylalkylamine oxide; addition ethylene oxide amine.

Procedures for the prepn of bis(hydroxyethyl)alkylamine oxides are presented. The solubilities and DTA of a number of amine oxides are also reported.

Abhandlungen der Akademie der Wissenschaften der DDR, Abteilung Mathematik, Naturwissenschaften, Technik published new progress about Addition reaction. 18312-57-7 belongs to class ethers-buliding-blocks, and the molecular formula is C17H37NO2, Recommanded Product: 2,2′-(Tridecylazanediyl)diethanol.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Niwa, Hideaki; Watanabe, Chiduru; Sato, Shin; Harada, Toshiyuki; Watanabe, Hisami; Tabusa, Ryo; Fukasawa, Shunsuke; Shiobara, Ayane; Hashimoto, Tomoko; Ohno, Osamu; Nakamura, Kana; Tsuganezawa, Keiko; Tanaka, Akiko; Shirouzu, Mikako; Honma, Teruki; Matsuno, Kenji; Umehara, Takashi published the artcile< Structure-Activity Relationship and In Silico Evaluation of cis- and trans-PCPA-Derived Inhibitors of LSD1 and LSD2>, HPLC of Formula: 6482-24-2, the main research area is phenylcycloproylamine preparation diastereoselective SAR anticancer enzyme inhibitor activity.

Synthesis of 65 cis- and trans-PCPA derivatives I [R = R1 = H, F; R2 = H, Cl, Me, etc.; R3 = H, F, OH; R4 = H, Br, CF3, etc.] and evaluated their inhibitory activity against LSD1 and LSD2 were reported. One of the derivatives, I [R = R3 = H, R1 = R2 = F, R4 = Br] inhibited LSD1 and LSD2 with Ki values of 0.094μM and 8.4μM, resp., and increased the level of dimethylated histone H3 at K4 in CCRF-CEM cells. A machine learning-based regression model (Q2 = 0.61) to predict LSD1-inhibitory activity was also constructed and showed a good prediction accuracy (R2 = 0.81) for I. The present methodol. would be useful when designing covalent-binding inhibitors for other enzymes.

ACS Medicinal Chemistry Letters published new progress about Antitumor agents. 6482-24-2 belongs to class ethers-buliding-blocks, and the molecular formula is C3H7BrO, HPLC of Formula: 6482-24-2.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Zhu, Yuchao; Zhang, Ziyao; Jin, Rui; Liu, Jianzhong; Liu, Guoquan; Han, Bing; Jiao, Ning published the artcile< DMSO-Enabled Selective Radical O-H Activation of 1,3(4)-Diols>, Quality Control of 6482-24-2, the main research area is diol silver DMSO aryl migration catalyst; ether keto preparation; DMSO; alkoxyl radicals; cleavage reactions; selectivity; silver.

Control of selectivity is one of the central topics in organic chem. Although unprecedented alkoxyl-radical-induced transformations have drawn a lot of attention, compared to selective C-H activation, selective radical O-H activation remains less explored. Herein, we report a novel selective radical O-H activation strategy of diols by combining spatial effects with proton-coupled electron transfer (PCET). It was found that DMSO is an essential reagent that enables the regioselective transformation of diols. Mechanistic studies indicated the existence of the alkoxyl radical and the selective interaction between DMSO and hydroxyl groups. Moreover, the distal C-C cleavage was realized by this selective alkoxyl-radical-initiation protocol.

Angewandte Chemie, International Edition published new progress about Aliphatic alcohols, radicals Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 6482-24-2 belongs to class ethers-buliding-blocks, and the molecular formula is C3H7BrO, Quality Control of 6482-24-2.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Leed, Andrew R.; Boettger, Susan D.; Ganem, Bruce published the artcile< Studies on the synthesis of substituted phenanthrenoids>, Reference of 56724-03-9, the main research area is juncusol; phenanthrene substituted; halogenation regioselective benzene.

Highly regioselective reactions for the construction of polysubstituted benzenes I (R = H, Me, SiMe2CMe3; R1, R2 = H, Br) and II (R3 = CO2H, CH2OH, CH2Br, CH2PPh3Br) are described, including some remarkable site-selective halogenations. These were used to prepare halo-, nitro-, amino-, and urethane-substituted stilbenes e.g., (E)-III (R4 = NO2, NH2, NHCO2Et; R5, R6 = H, iodo). Thermal as well as photochem. cyclizations were attempted. Stilbene III (R4 = NO2, R5 = H, R6 = iodo) gave the IV (R7 = H, Br; R8 = NO2, NH2); likewise III (R4 = NHCO2Et, R5 = H, R6 = iodo) furnished two new tricyclics, IV (R7 = Br; R8 = NH2, NHCO2Et), whereas irradiation of III (R4 = NHCO2Et, R5 = R6 = H) in HOCMe3 captured solvent to produce phenanthrenes IV (R7 = NHCO2Et; R8 = OH, OCMe3). Strategies for the total synthesis of juncusol (V), a cytotoxic phytoalexin, are considered.

Journal of Organic Chemistry published new progress about Halogenation, regioselective. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Reference of 56724-03-9.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Liu, Yu; Cornella, Josep; Martin, Ruben published the artcile< Ni-Catalyzed Carboxylation of Unactivated Primary Alkyl Bromides and Sulfonates with CO2>, Application of C11H16O2, the main research area is nickel catalyzed carboxylation primary alkyl bromide sulfonate carbon dioxide; carboxylic acid synthesis.

A Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2 at atm. pressure is described. The method is characterized by its mild conditions and remarkably wide scope without the need for air- or moisture-sensitive reagents, which make it a user-friendly and operationally simple protocol en route to carboxylic acids. Thus, e.g., reductive carboxylation 1-bromo-6-(4-methoxyphenyl)hexane using NiCl2.glyme, 2,9-diethyl-1,10-phenanthroline ligand, Mn as reducing agent and CO2 afforded 7-(4-methoxyphenyl)heptanoic acid in 76% isolated yield.

Journal of the American Chemical Society published new progress about Bromoalkanes Role: RCT (Reactant), RACT (Reactant or Reagent) (primary). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Application of C11H16O2.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Jagannadham, Y.; Ramadevi, B.; Prasanna, B. published the artcile< An improved economical process for preparation of apremilast and identified their impurities>, Related Products of 608141-42-0, the main research area is acetamidophthalic acid ethoxy methoxyphenyl methylsulfonyl ethylamine cyclocondensation; apremilast preparation.

An improved and com. viable process provided for the preparation of apremilast, which was simple, cost effective and non-hazardous. The usage of acetic anhydride and high temperature was avoided. An alternative process using protected 3-aminophthalic acid with acetyl chloride in the presence of triethanolamine as catalyst in dichloromethane solvent at 0 to 5° for 1 h. then followed by condensed with (S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine to get the final apremilast product was reported. Besides, there were two unknown impurities like 3-(amino-1,3-dioxoisoindolin-2-yl)phthalic acid and 4-aminoisobenzofuran-1,3-dione identified by HPLC. A thorough study was under taken to synthesize and characterize these unknown impurities. This improved process has a number of industrial advantages, such as economical material cost and relatively high yield. The structure of the synthesized compounds was elucidated by IR, 1H NMR, 13C NMR, mass spectroscopy and elemental analyses.

Asian Journal of Chemistry published new progress about Cyclocondensation reaction. 608141-42-0 belongs to class ethers-buliding-blocks, and the molecular formula is C12H19NO4S, Related Products of 608141-42-0.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem