132910-78-2Relevant articles and documents
Discovery and Total Synthesis of Streptoaminals: Antimicrobial [5,5]-Spirohemiaminals from the Combined-Culture of Streptomyces nigrescens and Tsukamurella pulmonis
Sugiyama, Ryosuke,Nishimura, Shinichi,Ozaki, Taro,Asamizu, Shumpei,Onaka, Hiroyasu,Kakeya, Hideaki
, p. 10278 - 10282 (2016)
A series of lipidic spirohemiaminals, designated streptoaminals, is reported. These were discovered by surveying the unique molecular signatures identified in the mass spectrometry data of the combined-culture broth of Streptomyces nigrescens HEK616 and T
A stereospecific synthesis and unambiguous assignment of the absolute configuration of (-)-erythro-Mefloquine hydrochloride
Zhou, Gang,Liu, Xian,Liu, Xueying,Nie, Huifang,Zhang, Shengyong,Chen, Weiping
, p. 3575 - 3580 (2013)
(-)-erythro-Mefloquine hydrochloride was synthesized stereospecifically from commercially available (S)-(-)-1-Boc-2-piperidinecarboxylic acid in four steps without disturbing the chiral center, and the absolute configuration of (-)-erythro-mefloquine hydrochloride was unambiguously determined as (11R,12S). (11S,12R)-(+)-erythro-Mefloquine hydrochloride was synthesized utilizing [(S,S)-TsDpen]Ru(p-cymene)Cl complexes-catalyzed enantioselective transfer hydrogenation of pyridyl ketone 7 as the key step, and the sense of asymmetric induction of 2-pyridyl ketone 7 is opposite to that of normal ketones in the transfer hydrogenation. Our results confirm the correctness of the determination of the absolute configuration by three physical chemistry methods, and, unbelievably, the erroneous assignments by all previous five asymmetric syntheses. Copyright
Racemic and enantiopure 4-(piperidine-2′-yl)-pyridazines: Novel synthesis of anabasine-analogues with potential nicotinic acetylcholine receptor agonist activity - A new approach via Diels-Alder reaction with inverse electron demand
Stehl, Astrid,Seitz, Gunther,Schulz, Karen
, p. 1343 - 1354 (2002)
A novel multistep synthesis of anabasine analogues bearing a bioisosteric pyridazine moiety instead of a pyridine nucleus in 2-position of the piperidine ring of the alkaloid is described. Starting materials are racemic 2-hydroxymethyl-piperidine, racemic pipecolic acid or (S)-(-)-piperidine-1,2-dicarboxylic-acid-1-tert-butyl ester. Key step of this synthetic approach is a Diels-Alder cycloaddition process with inverse electron demand utilizing diverse 1,2,4,5-tetrazines as electron-deficient dienes and the new racemic or enantiopure 2-(2′-methoxyethenyl)-piperidine as electron-rich dienophile. In this [4+2]-cycloadditions 1,2,4,5-tetrazines serve as synthons for introducing the pyridazine ring in the 2-position of the piperidine moiety.
Synthesis of a model compound of corydendramine a via a julia coupling
McCrea-Hendrick, Maddy,Nichols, Christopher J.
, p. 3611 - 3620 (2009)
The synthesis of the tetraenylpiperidine 12, which has the same core structure as the natural product corydendramine A, has been completed in eight steps starting from 2-piperidinemethanol 3 and trans,trans-2,6-nonadienal 6. The key step of the synthesis was a Julia coupling of sulfone (10) with aldehyde (5) to form a conjugated triene.
A fit for purpose synthesis of Bruton's tyrosine kinase inhibitor GDC-0852
Lim, Ngiap-Kie,Zhang, Haiming,Sowell, C. Gregory,Gosselin, Francis
, (2020)
The development of an expedient synthesis to GDC-0852 (1), a reversible BTK inhibitor drug candidate, is described. The key starting material tricyclic lactam 5 was prepared by an annulation reaction of unprotected piperidine-2-carbaldehyde HCl salt (20) and N-Boc piperidine-2,4-dione 21 in a safe and scalable manner. A highly selective Pd-catalyzed C[sbnd]N coupling of lactam 5 and linker 2a, followed by Suzuki?Miyaura coupling to fragment 8 subsequently provided a direct and convergent access to the penultimate 17. A simple NaBH4 aldehyde reduction completed the synthesis to GDC-0852 (1) in high yield (54% over 3 steps from 5) and purity (99.0 A% HPLC).
X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease
Ning, Xiang-Li,Li, Yu-Zhi,Huo, Cui,Deng, Ji,Gao, Cheng,Zhu, Kai-Rong,Wang, Miao,Wu, Yu-Xiang,Yu, Jun-Lin,Ren, Ya-Li,Luo, Zong-Yuan,Li, Gen,Chen, Yang,Wang, Si-Yao,Peng, Cheng,Yang, Ling-Ling,Wang, Zhou-Yu,Wu, Yong,Qian, Shan,Li, Guo-Bo
, p. 8303 - 8332 (2021/06/30)
Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.
A One-Pot Iodo-Cyclization/Transition Metal-Catalyzed Cross-Coupling Sequence: Synthesis of Substituted Oxazolidin-2-ones from N-Boc-allylamines
Chaumont-Olive, Pauline,Cossy, Janine
supporting information, (2020/05/14)
A one-pot iodo-cyclization/transition metal-catalyzed cross-coupling sequence is reported to access various C5-functionalized oxazolidin-2-ones from unsaturated N-Boc-allylamines. Depending on the Grignard reagents used for the cross-coupling, e.g., aryl- or cyclopropylmagnesium bromide, a cobalt or copper catalyst has to be used to obtain the functionalized oxazolidin-2-ones in good yields.
Compound, preparation method thereof, pharmaceutical composition and application of compound
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, (2020/01/03)
The invention discloses a compound, a preparation method thereof, a pharmaceutical composition and application of the compound. The compound I, and a stereoisomer or a pharmacologically acceptable salt thereof can serve as a CDK7 kinase inhibitor, are high in inhibition activity, and can be used for treatment of various malignant tumors.
COMPOUNDS, COMPOSITIONS AND METHODS FOR SYNTHESIS
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, (2019/01/10)
The present disclosure, among other things, provides technologies for synthesis, including reagents and methods for stereoselective synthesis. In some embodiments, the present disclosure provides compounds useful as chiral auxiliaries. In some embodiments, the present disclosure provides reagents and methods for oligonucleotide synthesis. In some embodiments, the present disclosure provides reagents and methods for chirally controlled preparation of oligonucleotides. In some embodiments, technologies of the present disclosure are particularly useful for constructing challenging internucleotidic linkages, providing high yields and stereoselectivity.
Protecting-Group-Directed Regio- and Stereoselective Oxymercuration-Demercuration: Synthesis of Piperidine Alkaloids Containing 1,2- and 1,3-Amino Alcohol Units
Bugde, Sandesh T.,Volvoikar, Prajesh S.,Tilve, Santosh G.
, p. 1113 - 1122 (2017/12/06)
An efficient synthesis of naturally occurring 1,2- and 1,3-amino alcohol unit containing 2-substituted piperidine alkaloids and their analogues has been developed from l -pipecolinic acid. The protocol describes the regio- and stereoselective oxymercuration-demercuration of 2-alkenyl piperidines based on protecting groups to give piperidine alkaloids as a key step.
