Month: December 2022

Yousif, M. N. M. published the artcileSynthesis and Anticancer Activity of New Substituted Piperidinones Linked to Pyrimidine, Thiazole, and Triazole Glycoside Derivatives, Computed Properties of 826-36-8, the publication is Russian Journal of General Chemistry (2019), 89(8), 1673-1682, database is CAplus.

New piperidinone incorporating pyrimidine, triazine, diazipine, oxatriazine, and thiazole derivatives have been synthesized starting with tetramethylpipridin-4-one. Structures of the newly synthesized compounds are characterized on the basis of spectroscopic and anal. data. The anticancer activity of the prepared compounds has been studied in vitro against HCT-116 and MCF-7 human cancer cells using the MTT assay. A number of compounds demonstrates potent activity towards both cell lines with IC₅₀ values comparable with doxorubicin.

Russian Journal of General Chemistry published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C17H37NO3, Computed Properties of 826-36-8.

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

Salome, Christophe published the artcileBenzofuran derivatives as a novel class of inhibitors of mTOR signaling, Recommanded Product: Piperidine-4-carboxamide, the publication is European Journal of Medicinal Chemistry (2014), 41-49, database is CAplus and MEDLINE.

High-throughput screening (HTS) hit (I) was previously identified as an inhibitor of the Akt/mTOR (Akt/mammalian target of rapamycin) signaling, which is a major target in oncol. The cytotoxicity of I was determined on a panel of human cancer cells lines with an IC₅₀ comprised between 30 and 140 μM. Subsequent structure-activity relation (SAR) studies led us to the identification of compounds that displayed an enhanced cytotoxicity. We demonstrated also that these mols. directly bind to mTOR complex 1 (mTORC1) and inhibit its kinase activity.

European Journal of 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, Recommanded Product: Piperidine-4-carboxamide.

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

Yu, V. K. published the artcileEsters of 1-(alkoxyalkyl)-4-piperidinols, SDS of cas: 512778-95-9, the publication is Izvestiya Ministerstva Obrazovaniya i Nauki Respubliki Kazakhstan, Natsional’noi Akademii Nauk Respubliki Kazakhstan, Seriya Khimicheskaya (2002), 70-76, database is CAplus.

4-Piperidinols I (n = 2, R = Me, Et; n = 3, R = Bu, decyl) were prepared by NaBH₄ reduction of the 4-piperidinones. I were esterified with acid chlorides and anhydrides to give the acetates, propanoates, and benzoates, all isolated as the hydrochlorides. The benzoate hydrochlorides exhibited higher local anesthetic activity than lidocaine.

Izvestiya Ministerstva Obrazovaniya i Nauki Respubliki Kazakhstan, Natsional’noi Akademii Nauk Respubliki Kazakhstan, Seriya Khimicheskaya published new progress about 512778-95-9. 512778-95-9 belongs to piperidines, auxiliary class Piperidine,Alcohol,Ether, name is 1-(2-Methoxyethyl)piperidin-4-ol, and the molecular formula is C12H10O4S, SDS of cas: 512778-95-9.

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

Tarumoto, Yusuke published the artcileChemical inhibition of SIK3 as a therapeutic strategy in acute myeloid leukemia, Product Details of C32H34ClN7O3, the publication is Ketsueki Naika (2020), 81(4), 529-534, database is CAplus.

A review. Acute myeloid leukemia AML, a type of hematopoietic aneurysm, is caused by an excessive increase in undifferentiated bone marrow cells. These results suggest that SIK drugs can selectively suppress AML proliferation, indicating that SIK blockade is a candidate for an effective AML treatment strategy. Results show chem. inhibition of SIK3 as therapeutic strategy in acute myeloid leukemia.

Ketsueki Naika published new progress about 1936529-65-5. 1936529-65-5 belongs to piperidines, auxiliary class Immunology/Inflammation,SIK, name is 3-(2-Chloro-6-methylphenyl)-7-((2-methoxy-4-(1-methylpiperidin-4-yl)phenyl)amino)-1-(5-methoxypyridin-2-yl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one, and the molecular formula is C2H2N3NaS, Product Details of C32H34ClN7O3.

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

Sklavounos, Constantine published the artcileD-α-Aminoadipic acid from cephalosporin C, Computed Properties of 72002-30-3, the publication is Organic Preparations and Procedures International (1984), 16(3-4), 165-9, database is CAplus.

The title compound (I) ([α]_D²⁵ = -25.7°, 2% 6N HCl) was prepared by deacylating cephalosporin C via the imino chloride and imino ether to give Me D-α-aminoadipate which was converted to lactam by treatment of base, crystallized, and hydrolyzed to I.

Organic Preparations and Procedures International 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 C11H8O3, Computed Properties of 72002-30-3.

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

Reitsema, Robert H. published the artcileNovel rearrangement of a piperidine ring, Application In Synthesis of 13444-24-1, the publication is Journal of the American Chemical Society (1949), 2041-3, database is CAplus.

cf. C.A. 43, 6206i. 1-Ethyl-3-chloropiperidine-HCl (I) (18.4 g.) and 21.4 g. PhCH₂NH₂ in 20 cc. H₂O, heated 48 hrs. at 65-75°, give 73.4% 1-ethyl-2-(benzylaminomethyl)pyrrolidine (II), b₁ 134° (dipicrate, m. 190-1°). 1-Methyl-3-chloropiperidine yields 42% of the 1-Me homolog of II, b_0.2-0.3 110-12° (dipicrate, m. 172-3°). II (2.18 g.) in 50 cc. absolute EtOH, shaken overnight with 2 g. Pd-C (but not with Pt oxide) at 50°, gives 1-ethyl-2-(aminomethyl)pyrrolidine (III), whose dipicrate m. 177-8.5°; III results also from I and alc. NH₃ (20 days at room temperature). I (16 g.), 30.2 g. 8-amino-6-methoxyquinoline, and 25 cc. H₂O, heated 20 hrs. at 60-70° and 2 hrs. at 110°, give 9.1 g. 6-methoxy-8-(1-ethyl-2-pyrrolidylmethylamino)quinoline (IV), b_0.2 186-90°, whose di-HCl salt m. 214-16°, and dipicrate m. 202.5-3.5°. 1-Ethyl-3-piperidone, reduced in MeOH over Raney Ni at 125° and 2270 lb., gives 1-ethyl-3-hydroxypiperidine, whose benzoate-HCl m. 197-8°. IV is less effective for clinical use than many of the new antimalarials.

Journal of the American Chemical Society 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 In Synthesis of 13444-24-1.

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

Paul, Raymond published the artcileDerivatives of 3-hydroxypiperidine, Recommanded Product: 1-Ethylpiperidin-3-ol, the publication is Compt. rend. (1945), 221(No. 15), 412-14, database is CAplus.

1,2-Epoxy-5-chloropentane (I) reacts with amines in most cases to form piperidine derivatives I and 1 mol. NHEt₂ at 100° form a colorless solid, apparently the 1-ethyl-3-hydroxypiperidine-EtCl (II). II warmed with concentrated KOH gives C₂H₄ and 1-ethyl-3-hydroxypiperidine (III), b₂₁ 97-98°, d₁₅²³ 0.966, n_D²³ 1.47427 (77% yield based on I). The intermediate 1-diethylamino-5-chloropentane is not isolated. N,N-Diethyltetrahydrofurfurylamine reacts with dry HBr to form a water-soluble product, which reacts with NH₃ to form the ethobromide (IV) of III. IV warmed with concentrated KOH gave C₂H₄ and 74% of III. I and EtNH₂ at 100° form a product which reacts in hot KOH solution to give 74% of III. BzCl and III form the HCl salt of the benzoate ester, colorless needles, m. 204° and possessing marked anesthetic properties. III and excess concentrated HCl at 150° or III and 1 mol. SOCl₂ at 100-120° give 1-ethyl-3-chloropiperidine (V), colorless liquid of moldy odor, b₂₀ 75°, d₁₅^19.5 0.996, n_D^19.5 1.46807. Picrate of V m. 156-7°; methiodide, m. about 210 °. Aniline and 1 mol. I give at 120° 1-phenyl-3-hydroxypiperidine, colorless liquid, b₁₆ 176°, d₁₆¹⁵ 1.099, n_D¹⁵ 1.57856, and not N-phenyltetrahydrofurfurylamine (VI), b₁₀ 155-6°, d₁₆¹¹ 1.075, n_D¹¹ 1.56456, which was obtained by the action of aniline and tetrahydrofurfuryl chloride (VII) at 150°. The piperidine ring is not always formed, as shown by the action of PhNHEt on I for 12 h. at 125°. N-Tetrahydrofurfuryl-N-ethylaniline (VIII), b₂₀ 176-7°, d₁₆²² 1.052, n_D²² 1.55962, was formed. VIII was also obtained by direct action of PhNHEt on VII.

Compt. rend. 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, Recommanded Product: 1-Ethylpiperidin-3-ol.

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

Mitchell, Robin E. published the artcileSynthesis of amino acid conjugates to 2-imino-3-methylene-5-carboxypyrrolidine and 2-imino-3-methylene-6-carboxypiperidine, Recommanded Product: (R)-6-Oxopiperidine-2-carboxylic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(6), 1910-1912, database is CAplus and MEDLINE.

The four stereomers of 2-imino-3-methylene-5-(carboxy-L-valyl)pyrrolidine, a bacterial metabolite that is inhibitory to the fire blight bacterium Erwinia amylovora, were synthesized and compared for antibacterial activity. Several alternative amino acid conjugates with L,L-stereochem. were also prepared, and the synthesis was extended to 3-methylenepiperidine-6-L-carboxylic acid and a selection of 2-imino-3-methylenepiperidine-6-L-carboxy-L-amino acid conjugates. All synthetic amino acid conjugates (L,L-stereomers) were inhibitory to the growth of E. amylovora. The likely participation of the conjugated iminomethylene moiety as a Michael acceptor is implicated.

Bioorganic & Medicinal Chemistry Letters 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 C6H9NO3, Recommanded Product: (R)-6-Oxopiperidine-2-carboxylic acid.

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

Manap, Sevda published the artcileSynthesis and in vitro antioxidant and antimicrobial activities of novel 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones, and their N-acetyl, N-Mannich base derivatives, COA of Formula: C6H12N2O, the publication is Journal of the Iranian Chemical Society (2022), 19(4), 1347-1368, database is CAplus.

The reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones I (R = Me, Ph, Bn, etc.) with 3-methoxy-4-(2-furylcarbonyloxy)-benzaldehyde formed 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones II (R¹ = H). Moreover, their five N-acetyl derivatives II (R¹ = acetyl) were synthesized. Besides, compounds II (R¹ = morpholin-4-yl-methyl)/II (R¹ = N-methylpiperazinyl)/II (R¹ = (4-carbamoylpiperidin-1-yl)methyl)/III were obtained by Mannich reaction between compounds II (R¹ = H) and morpholine/N-methylpiperazine/piperidine-4-carboxyamide/piperazine in the presence of formaldehyde. Also, these compounds were evaluated for their in vitro antioxidant activity. Furthermore, in vitro antibacterial activity of the compounds was screened against six bacteria.

Journal of the Iranian Chemical Society 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

Deguchi, Yoshio published the artcilePiperidine derivatives, Computed Properties of 14613-37-7, the publication is Iyaku Shigen Kenkyusho Nempo (1956), 17-22, database is CAplus.

Dialkylureido-N-methylpiperidines and dialkylureidomethyl-N-methylpiperidines were prepared Pyridine-3-carboxylic acid amide (10 g.) is refluxed with 17.5 g. MeI and 30 cc. MeOH for 5 hrs., evaporated, the residue is dissolved in 30 cc. H₂O, warmed with freshly prepared AgCl (prepared from 20 g. AgNO₃ and 7 g. NaCl) for 3 hrs., and filtered. The filtrate is decolorized with active C and then catalytically reduced with 0.1 g. PtO₂ to give 85% N-methylpiperidine-3-carboxamide (I); hydrochloride m. 232° (alc.). Similarly was prepared N-methylpiperidine-4-carboxamide; hydrochloride, hygroscopic. A mixture of 7 g. I and 7 g. P₂O₅ is heated at 160-180° for 3 hrs., cooled, dissolved in 50 cc. H₂O with warming, neutralized with K₂CO₃, salted out, and the separated oil extracted with AcOEt to give 80% 3-cyano-N-methylpiperidine (II), b₂₀ 95-6°. Similarly was prepared 4-cyano-N-methylpiperidine, b₂₁ 97°. Into a cooled mixture of 1.3 g. LiAlH₄ and 150 cc. Et₂O is dropped a solution of 5.0 g. II in 50 cc. Et₂O during 90 min., the mixture stirred 1 hr., refluxed 30 min., 15 cc. H₂O added to decompose excess LiAlH₄, and filtered. The filtrate is dried with KOH, evaporated, and distilled in vacuo to give 90% 3-aminomethyl-N-methylpiperidine (III), b₂₀ 81-2°; dipicrate m. 231° (decomposition). Similarly was prepared 4-aminomethyl-N-methylpiperidine (IV), b₂₀ 80-1°; dipicrate m. 236° (decomposition). To a mixture of 32 g. KOH, 6.4 g. Br, and 400 cc. H₂O is dropped an aqueous solution of 5.7 g. I under ice cooling, then warmed at 70° for 1 hr., alkalized with KOH, distilled with steam, and the distilled solution treated with diluted HCl, concentrated in vacuo, alkalized with KOH, extracted with Et₂O, and the extract evaporated and distilled in vacuo to give 65% 3-amino-N-methylpiperidine (V), b₄₃ 74-5°; dipicrate m. 227° (decomposition). Similarly was prepared 4-amino-N-methyl-piperidine (VI), b₃₅ 70-1°; dipicrate m. 263° (decomposition). A mixture of 0.6 mole Me₂NH and 200 cc. PhMe is dropped into 50% phosgene-PhMe, refluxed 1 hr., and distilled in vacuo to give 40% dimethylcarbamoyl chloride (VII), b_55-60 85-8°. Similarly was prepared diethylcarbamoyl chloride (VIII), b_17-20 80°. A mixture of 2 moles III and 1 mole VII in Et₂O is kept at room temperature 1.5 hrs., refluxed 10 min., cooled, and filtered. The filtrate is evaporated and chromatographed using alumina to give 3-dimethylureidomethyl-N-methyl-piperidine, needles (petr.-ether), m. 66-9° (hygroscopic). Similarly were prepared following IX (starting materials, position of substituent, n, R, appearance, and m.p. given): III and VIII, 3, 1, Et, sirupy, -; IV and VII, 4, 1, Me, needles (hygroscopic), 40-4° (hydrochloride m. 230°); IV and VIII, 4, 1, Et, columns, 66-8°; V and VIII, 3, 0, Me, needles, 110-12°; V and VIII, 3, 1, Et, sirupy, (picrolonate m. 195-7°); VI and VII, 4, 0, Me, flakes, 138-9°; VI and VIII, 4, 0, Et, needles, 89-90°.

Iyaku Shigen Kenkyusho Nempo 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, Computed Properties of 14613-37-7.

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