Tag: M.W=100-150

Mizukawa, Yuki published the artcileQuest for a potent antimalarial drug lead: Synthesis and evaluation of 6,7-dimethoxyquinazoline-2,4-diamines, Safety of Piperidine-4-carboxamide, the publication is Bioorganic & Medicinal Chemistry (2021), 116018, database is CAplus and MEDLINE.

Quinazolines have long been known to exert varied pharmacol. activities that make them suitable for use in treating hypertension, viral infections, tumors, and malaria. Since 2014, author’s have synthesized approx. 150 different 6,7-dimethoxyquinazoline-2,4-diamines and evaluated their antimalarial activity via structure-activity relationship studies. Here, author’s summarize the results and report the discovery of 6,7-dimethoxy-N4-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-amine, which exhibits high antimalarial activity as a promising antimalarial drug lead.

Bioorganic & Medicinal Chemistry published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, Safety of Piperidine-4-carboxamide.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

He, Yantao published the artcileA potent and selective inhibitor for the UBLCP1 proteasome phosphatase, Computed Properties of 39546-32-2, the publication is Bioorganic & Medicinal Chemistry (2015), 23(12), 2798-2809, database is CAplus and MEDLINE.

The ubiquitin-like domain-containing C-terminal domain phosphatase 1 (UBLCP1) has been implicated as a neg. regulator of the proteasome, a key mediator in the ubiquitin-dependent protein degradation Small mol. inhibitors that block UBLCP1 activity would be valuable as research tools and potential therapeutics for human diseases caused by the cellular accumulation of misfold/damaged proteins. The authors report a salicylic acid fragment-based library approach aimed at targeting both the phosphatase active site and its adjacent binding pocket for enhanced affinity and selectivity. Screening of the focused libraries led to the identification of the first potent and selective UBLCP1 inhibitor I. Compound I exhibits an IC₅₀ of 1.0 μM for UBLCP1 and greater than 5-fold selectivity against a large panel of protein phosphatases from several distinct families. Importantly, the inhibitor possesses efficacious cellular activity and is capable of inhibiting UBLCP1 function in cells, which in turn up-regulates nuclear proteasome activity. These studies set the groundwork for further developing compound I into chem. probes or potential therapeutic agents targeting the UBLCP1 phosphatase.

Bioorganic & Medicinal Chemistry published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, Computed Properties of 39546-32-2.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Szokan, Gy. published the artcileHPLC determination of enantiomeric purity of protected amino acid derivatives used in peptide synthesis, Recommanded Product: (R)-6-Oxopiperidine-2-carboxylic acid, the publication is Journal of Liquid Chromatography (1994), 17(13), 2759-75, database is CAplus.

An improved RP-HPLC method on ODS-Hypersil column with precolumn derivatization with Marfey’s reagent was used to monitor racemization in N-, C- and/or side-chain protected amino acid derivatives by separation of new diastereoisomeric Marfey’s compounds Chromatog. samples were obtained by partial deprotection of different starting materials. In a simple two-step procedure (deprotection and derivatization) the compounds of amino acids formed stable diastereomeric derivatives having facile resolutions

Journal of Liquid Chromatography published new progress about 72002-30-3. 72002-30-3 belongs to piperidines, auxiliary class Piperidine,Chiral,Carboxylic acid,Amide, name is (R)-6-Oxopiperidine-2-carboxylic acid, and the molecular formula is C15H16O3, Recommanded Product: (R)-6-Oxopiperidine-2-carboxylic acid.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Peter Ventura, Alejandra M. published the artcileDevelopment of Biarylalkyl Carboxylic Acid Amides with Improved Anti-schistosomal Activity, COA of Formula: C6H12N2O, the publication is ChemMedChem (2019), 14(21), 1856-1862, database is CAplus and MEDLINE.

The parasitic disease schistosomiasis is the cause of more than 200 000 human deaths per yr. Although the disease is treatable, there is one major shortcoming: praziquantel has been the only drug used to combat these parasites since 1977. The risk of the emergence of resistant schistosomes is known to be increasing, as a reduced sensitivity of these parasites toward praziquantel has been observed We developed a new class of substances, which are derived from inhibitors of human aldose reductase, and which showed promising activity against Schistosoma mansoni couples in vitro. Further optimization of the compounds led to an increase in anti-schistosomal activity with observed phenotypes such as reduced egg production, vitality, and motility as well as tegumental damage and gut dilatation. Here, we performed structure-activity relationship studies on the carboxylic acid moiety of biarylalkyl carboxylic acids. Out of 82 carboxylic acid amides, we identified 10 compounds that are active against S. mansoni at 25 μm. The best five compounds showed an anti-schistosomal activity up to 10 μm and induced severe phenotypes. Cytotoxicity tests in human cell lines showed that two derivatives had no cytotoxicity at 50 or 100 μm. These compounds are promising candidates for further optimization toward the new anti-schistosomal agents.

ChemMedChem published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, COA of Formula: C6H12N2O.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Mueller, Stephan G. published the artcileDesign, synthesis and evaluation of MCH receptor 1 antagonists-Part I: Optimization of HTS hits towards an in vivo efficacious tool compound BI 414, HPLC of Formula: 39546-32-2, the publication is Bioorganic & Medicinal Chemistry Letters (2015), 25(16), 3264-3269, database is CAplus and MEDLINE.

Despite recent approvals of antiobesity drugs there is still a high therapeutic need for alternative options with higher efficacy in humans. As part of the MCH-R1 antagonist program for the treatment of obesity, a series of biphenylacetamide HTS hits was evaluated. Several issues of the initial lead structures had to be resolved, such as potency, selectivity over related GPCRs and P-gp efflux limiting brain exposure in this series. The authors could demonstrate that all parameters can be significantly improved by structural modifications resulting in I as a potent and orally available MCH-R1 antagonist tool compound with acceptable in vivo efficacy in an animal model of obesity.

Bioorganic & Medicinal Chemistry Letters published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, HPLC of Formula: 39546-32-2.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Abdel-Rahman, M. O. published the artcileHeterocyclic aminoacrylate esters of potential biological activity, Product Details of C7H15NO, the publication is Qatar University Science Bulletin (1985), 63-9, database is CAplus.

Acrylate esters I and II (X = O, S; R = N-methyl-4-piperidyl, N-ethyl-4-piperidyl, N-methyl-3-piperidyl, N-ethyl-4-piperidyl, 3-quinuclidinyl, CH₂CH₂NMe₂, CH₂CH₂NEt₂) were prepared from the corresponding acids or acid chlorides and aminoalcs.

Qatar University Science Bulletin published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, Product Details of C7H15NO.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Hammer, C. F. published the artcileReactions of β-substituted amines. II. Nucleophilic displacement reactions on 3-chloro-1-ethylpiperidine, Quality Control of 13444-24-1, the publication is Tetrahedron (1972), 28(2), 239-53, database is CAplus.

Synthetic, kinetic, and optical activity studies established that 3-chloro-1-ethylpiperidine undergoes nucleophilic displacement reactions in solution by a 2-step, neighboring group participation mechanism. N displaces chloride internally, to give an ambident bicyclic aziridinium ion, which then reacts with nucleophiles to give pyrrolidine and piperidine isomers. The aziridinium ion, 1-ethyl-1-azoniabicyclo[3.1.0]hexane perchlorate, was synthesized sep.

Tetrahedron published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, Quality Control of 13444-24-1.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Hammer, Charles F. published the artcileIsolation of a bicyclic aziridinium ion intermediate, Application of 1-Ethylpiperidin-3-ol, the publication is Chemical Communications (London) (1966), 919-20, database is CAplus.

cf. Ebnoether and Jucker, CA 60, 15830b. 1-Azabicyclo [3.1.0]-hexane in dry Et2O and EtClO4 in absolute EtOH gave a semi-solid, extraction of which with CH2Cl2 gave a product whose N.M.R. spectrum was similar to the N.M.R. spectrum of the oil obtained from 3-chloro-N-ethylpiperidine and AgClO4 in dry Me2CO; and presumably, based on the spectrum, the product possesses the bicyclic aziridinium structure (I).

Chemical Communications (London) published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, Application of 1-Ethylpiperidin-3-ol.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Drefahl, G. published the artcileAmino alcohols. XX. Preparation of 1-substituted 2-piperidino-1-cyclohexanols, Product Details of C7H16N2, the publication is Journal fuer Praktische Chemie (Leipzig) (1966), 32(1-2), 69-86, database is CAplus.

cf. CA 64, 19600c. A series of cis- and trans-isomers of 1-substituted 2-piperidinocyclohexanols (I) was prepared 2-Chlorocyclohexanone (160 g.) added with stirring to refluxing 205 g. piperidine and 200 cc. MePh, heated 2 hrs. at 140° (bath), cooled, and treated with 300 cc. 5% NH₄OH yielded 85-90 g. 2-piperidinocyclohexanone (II), b₃ 95-7°; II.HCl, m. 202-5° (EtOH-dioxane). II (0.1 mole) in 150 cc. dry Et₂O added dropwise with cooling and stirring to 0.7 mole appropriate Grignard reagent in 250 cc. dry Et₂O under argon and heated 1-2 hrs. at about 50° yielded the corresponding cis-I. The Grignard derivative from 0.6 mole alkyl or aryl halide and 15 g. Mg in 250 cc. dry Et₂O treated under argon with stirring and cooling with 0.4 mole cyclohexanone in an equivalent amount Et₂O slowly during about 6-8 hrs. and kept overnight, and the crude product heated 2-3 hrs. at 130-150° in the presence of a few crystals iodine yielded the following 1-substituted cyclohexenes (substituent, b.p./mm., and % yield given): iso-Bu, 169-71°/750, 18; cyclopentyl, 87-9°/ 12, 32; p-cumenyl, 148-52°/13, 35; p-PhC₆H₄, 180-2°/1.5 [m.p. 145-6° (iso-PrOH-C₆H₆), greenish blue fluorescence]. The appropriate III in about 2 volumes dry Et₂O added with stirring and cooling to 0.5-0.6M o-HO₂CC₆H₄CO₂OH gave the corresponding 1-substituted 1,2-epoxycyclohexane (IV). The appropriate III (1 mole) added dropwise with stirring below 20° to 1 mole N-bromosuccinimide in 400 cc. H₂O containing 1 cc. AcOH, stirred about 1 hr., and evaporated, and the oily, black-brown residue added dropwise at room temperature to 1 equivalent absolute KOH-MeOH and heated 0.5 hr. at 60° (bath) gave the corresponding IV. By these methods were prepared the following IV (R and b.p./mm. given): H 36-9°/25, Me 37-9°/14, Et 51-3°/14, Pr 62-4°/12, Bu 41-4°/1, Am 75-80°/3, iso-Pr 59-62°/12, iso-Bu 47-51°/2-3, iso-Am 67-71°/2-3, tert-Bu 64-8°/13, cyclopentyl 102-3°/12, cyclohexyl 117-18°/12 (m. 10-11°), Ph 131-3°/12, PhCH₂ 136-8°/12, PhCH₂CH₂ 151-3°/12, p-MeC₆H₄ 90-5°/0.4, p-cumenyl 102-10°/0.5, o-MeC₆H₄ 79-84°/0.4, 1-C₁₀H₇ 138-42°/ 0.6 (m. 61-3°). R, b.p./mm., n²⁰_D, % yield, m.p. of HCl salt; Me, 83-4°/0.6, 1.4914, 69, 198-200° (EtOH-dioxane); Et, 114-15°/1.3, 1.4933, 46, 189-92° (Me₂CO-petroleum ether); Pr, 118-21°/1-1.1, 1.4895, 55, 163-6° (Me₂CO-petroleum ether); Bu, 127-8°/0.9, 1.4882, 38, 182-4° (Me₂CO); Am, 136-7°/0.8, 1.4871, 59, 191-4°; iso-Pr, 116-17°/1, 1.4944, 55, 208-10°; iso-Bu, 128-30°/1.6, 1.4874, 72, 193-5°; iso-Am, 132-3°/0.8, 1.4864, 73, 198-200°; tert-Bu, 118-19°/0.6, 1.4981, 21, 182-3°; cyclopentyl, 142-3°/0.7, 1.5111, 24, 220-2° (iso-PrOH); cyclohexyl, 151-2°/0.7 (m. 51-3°), 1.5103, 33, 231-3° (iso-PrOH); Ph, 158-60°/0.7 (m. 65-6°), 1.5423, 39, 237-9° (Bu₂O-EtOH); PhCH₂, 166-7°/0.6, 1.5432, 85, 234-6° (iso-PrOH); PhCH₂CH₂, 172-3°/0.5, 1.5362, 89, 210-12° (EtOH-dioxane); p-MeC₆H₄, 160-1°/0.8 (m. 54-5°), 1.5400, -, 247-9°; p-cumenyl, 168-9°/0.6, 1.5300, 66, 202-5° (iso-PrOH); p-PhC₆H₄, 214-18°/0.4 (m. 105-7°), -, 70, 231-4° (absolute EtOH); o-MeC₆H₄, 155-6°/0.6, 1.5398, 79, 265-6°; 1-C₁₀H₇, 204-5°/0.8 (m. 106-7°), -, 50, 220-3° (EtOH-Et₂O) The appropriate IV and excess piperidine in 95% EtOH heated in a sealed tube or in an autoclave gave the corresponding trans-I. The crude cis- or traus-I in the 8-10 fold amount dry Et₂O treated dropwise at 0-5° with the equivalent amount HCl-Et₂O yielded the I.HCl. II in EtOH hydrogenated 3 hrs. at 65°/65 atm. yielded 66% cis-I (R = H), m. 93-4° (50% EtOH); HCl salt, m. 287-8° (iso-PrOH). R, b.p./mm., m.p., n²⁰_D, % yield, m.p. of HCl salt, moles piperidine used/mole IV, reaction time (hrs.), temperature; H, 82-5°/0.5, 35-6°, 1.4890, 46, 263-6°, 5, 5-6, 130°; Me, 97-8°/1, 43-4°, 1.4887, 37, 263-4°, 5, 6-8, 150°; Et, 110-12°/1.3, -, 1.4886, 59, 233-4°, 5, 6-8, 150°; Pr, 122-5°/1-1.2, 63-4°, 1.4886, 45, 217-18°, 5, 6-8, 150°; Bu, 131-3°/1, 52-3°, 1.4875, 40, 225-7°, 5, 6-8, 150°; Am, 146-8°/1.3, 37-9°, 1.4862, 19, 232-3°, 5, 6-8, 150°; iso-Pr, 116-17°/1, -, 1.4944, 55, 211-13°, 5, 8-9, 150°; iso-Bu, 113-14°/0.6, -1.4857, 12, 230-2°, 5, 10-11, 150°; iso-Am, 127-8°/0.6, 48-50°, 1.4843, 56, -, 5, 6-8, 150°; tert-Bu, 132-4°/1.3, -, 1.5072, 3.5, 178-80°, 8, 11-12, 150°; cyclopentyl, 140-1°/0.5, -, 1.5108, 40, 168-71°, 5, 7-9, 160°; cyclohexyl, 150-1°/0.6, -, 1.5140, 55, 218-19°, 5, 11-12, 180°; Ph, 158-9°/0.8, -, 1.5471, 30, 216-18°, 5, 5-6, 150°; PhCH₂, -, 121-2°, -, 25, -, 5, 6-7, 150°; PhCH₂CH₂, -, 103-5°, -, 38, 239-41°, 5, 7-8, 160°; p-MeC₆H₄, 163-9°/0.4, 106-9°, -, 2.4, 284-6°, 8, 10-11, 175°; p-cumenyl, 150-3°/0.4, -, -, 2, 277-9°, 8, 10-11, 175°; o-MeC₅H₄, 135-6°/0.2, -, 1.5532, 3.7, 196-9°, 8, 9-10, 190°; 1-C₁₀H₇, 196-8°/0.3, 96-8°, -, 14, 166-9°, 15, 9-10, 220° By the general method described were prepared the cis-I listed in the 1st table. By the general method were prepared the trans-I listed in the 2nd table.

Journal fuer Praktische Chemie (Leipzig) published new progress about 14613-37-7. 14613-37-7 belongs to piperidines, auxiliary class Piperidine,Amine, name is (1-Methylpiperidin-3-yl)methanamine, and the molecular formula is C7H16N2, Product Details of C7H16N2.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Kumar, Adarsh published the artcileBiocarbon Supported Nanoscale Ruthenium Oxide-Based Catalyst for Clean Hydrogenation of Arenes and Heteroarenes, Product Details of C6H12N2O, the publication is ACS Sustainable Chemistry & Engineering (2020), 8(41), 15740-15754, database is CAplus.

Despite considerable achievements in the hydrogenation of aromatic hydrocarbons over the past few years, the ability to hydrogenate arene or heteroarene rings in a highly selective manner in the presence of other reducible sites or without harming the remaining mol. structure has long been a major challenge. Such chemoselectivity and functional group tolerance is highly desirable for enabling direct access to key building blocks of polymers and pharmaceutical agents. For achieving such high selectivity, the development of suitable catalysts is of central importance. Herein, we report a convenient method for the scalable preparation of ruthenium oxide (RuO₂) nanoparticles supported on pine needle char (PNC) by simple impregnation of ruthenium salt on unactivated PNC, a solid byproduct (biochar) obtained in the slow pyrolysis of biomass pine needles. The resulting RuO₂-based nanocatalyst (RuO₂@PNC) exhibited remarkable activity and high selectivity for the hydrogenation of more than 50 challenging arenes and heteroarenes, including biomass-derived aromatic compounds (e.g., 4-n-propylphenol, furfuryl alc., and 2-Me furan). The synthetic value of this transformation is showcased for the hydrogenation of arene mixture present in petroleum refineries or coal tars as well as biomass-derived oils (bio-oils) with enriched furfural, ether, and phenol derivatives Under optimized conditions, the performance of this new catalyst was compared with state-of-the-art com. catalysts such as Ru/C, Pd/C, and Raney nickel and found that RuO₂@PNC is more superior and selective. Furthermore, the catalyst is easily recovered and reused up to four cycles. Biocarbon supported RuO₂-based catalyst exhibited remarkable activity and selectivity for clean hydrogenation of arenes and heteroarenes.

ACS Sustainable Chemistry & Engineering published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, Product Details of C6H12N2O.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem