17012-21-4Relevant academic research and scientific papers
Aminoborohydrides. 11. Facile reduction of N-alkyl lactams to the corresponding amines using lithium aminoborohydrides
Flaniken, John M.,Collins, Christopher J.,Lanz, Marc,Singaram, Bakthan
, p. 799 - 801 (1999)
Formula presented Various five- and six-membered N-alkyl lactams were reduced to the corresponding cyclic amines using lithium N,N-dialkylaminoborohydrides (LAB). Most of the reductions were essentially complete after refluxing in THF for 2 h. The cyclic amine products were easily isolated after an aqueous workup in very good to excellent yields. It is possible to selectively reduce most functional groups, such as esters, in the presence of a lactam using LAB reagents.
Facile reduction of tertiary lactams to cyclic amines with 9- borabicyclo[3.3.1]nonane (9-BBN)
Collins, Christopher J.,Lanz, Marc,Singaram, Bakthan
, p. 3673 - 3676 (1999)
Various 5- and 6-membered tertiary lactams were reduced to the corresponding cyclic tertiary amines using 2.2 to 2.5 equivalents of 9- borabicyclo[3.3.1]nonane (9-BBN). This method is highly chemoselective and it is easy to reduce a lactam in the presence of an ester.
Discovery of the PARP (poly ADP-ribose polymerase) inhibitor 2-(1-(4,4-difluorocyclohexyl)piperidin-4-yl)-1H-benzo[d]imidazole-4-carboxamide for the treatment of cancer
Chen, Dawei,Jiang, Yuyang,Shi, Zhichao,Tang, Lin,Wu, Weibin,Zhai, Xin,Zhang, Cunlong
supporting information, (2021/07/28)
In this work, two series of cyclic amine-containing benzimidazole carboxamide derivatives were designed and synthesized as potent anticancer agents. PARP1/2 inhibitory activity assays indicated that most of the compounds showed significant activity. The in vitro antiproliferative activity of these compounds was investigated against four human cancer cell lines (MDA-MB-436, MDA-MB-231, MCF-7 and CAPAN-1), and several compounds exhibited strong cytotoxicity to tumor cells. Among them, 2-(1-(4,4-difluorocyclohexyl)piperidin-4-yl)-1H-benzo[d]imidazole-4-carboxamide (17d) was found to be effective PARP1/2 inhibitors (IC50 = 4.30 and 1.58 nM, respectively). In addition, 17d possessed obvious selective antineoplastic activity and noteworthy microsomal metabolic stability. What's more, further studies revealed that 17d was endowed with an excellent ADME profile. These combined results indicated that 17d could be a promising candidate for the treatment of cancer.
Discovery of 2-(1-(3-(4-Chloroxyphenyl)-3-oxo-propyl)pyrrolidine-3-yl)-1H-benzo[d]imidazole-4-carboxamide: A Potent Poly(ADP-ribose) Polymerase (PARP) Inhibitor for Treatment of Cancer
Min, Rui,Wu, Weibin,Wang, Mingzhong,Tang, Lin,Chen, Dawei,Zhao, Huan,Zhang, Cunlong,Jiang, Yuyang
, (2019/05/27)
A series of benzimidazole carboxamide derivatives have been synthesized and characterized by 1H-NMR, 13C-NMR and HRMS. PARP inhibition assays and cellular proliferation assays have also been carried out. Compounds 5cj and 5cp exhibited potential anticancer activities with IC50 values of about 4 nM against both PARP-1 and PARP-2, similar to the reference drug veliparib. The two compounds also displayed slightly better in vitro cytotoxicities against MDA-MB-436 and CAPAN-1 cell lines than veliparib and olaparib, with values of 17.4 μM and 11.4 μM, 19.8 μM and 15.5 μM, respectively. The structure-activity relationship based on molecular docking was discussed as well.
Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines
Chardon, Aurélien,Mohy El Dine, Tharwat,Legay, Rémi,De Paolis, Micha?l,Rouden, Jacques,Blanchet, Jér?me
supporting information, p. 2005 - 2009 (2017/02/19)
A reduction of various aryl, alkyl, and α,β-unsaturated amides with phenylsilane, catalysed by a borinic acid, is reported. The unprecedented reaction was carried out under very mild conditions and led to useful amines. Furthermore, the reaction tolerates a variety of functional groups. Initial investigations implicated that an intermediate diarylhydroborane is involved in the reaction mechanism.
With antifungal activity of the wicked zuozuo apperception compound and its preparation method and application (by machine translation)
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Paragraph 0036-0038, (2017/09/02)
The invention discloses an oxazole compound with anti-fungal activity, a preparation method of the oxazole compound and an application of the oxazole compound to tobacco powdery mildew original fungi or cotton anthracnose original fungi prevention, and belongs to the technical field of organic synthesis. The technical scheme mainly includes that the oxazole compound with the anti-fungal activity is provided with a structure shown in the instruction, R1 refers to propiono, isopropyl, acetyl, ethyl or methyl, and R2 refers to dimethylamino or methylamine. Five oxazole compounds with the anti-fungal activity are synthesized by the novel method, the preparation process is simple in technology and easy to control, target product yield is high, repeatability is fine, and the five prepared oxazole compounds with the anti-fungal activity have a certain prevention function for tobacco powdery mildew original fungi or cotton anthracnose original fungi.
Synthesis of Orthogonally Protected 2,6-Diazaspiro[35]nonane and 2,6-Diazaspiro[3.4]octane Analogues as Versatile Building Blocks in Medicinal Chemistry
Orain, David,Hintermann, Samuel,Pudelko, Maciej,Carballa, Diego,Jedrzejczak, Anna
supporting information, p. 1815 - 1818 (2015/08/06)
A novel and efficient synthesis of orthogonally protected spirocyclic amines is described for the first time.
(3,4-DICHLORO-PHENYL)-((S)-3-PROPYL-PYRROLIDIN-3-YL)-METHANONE HYDROCHLORIDE AND MANUFACTURING PROCESSES
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Paragraph 0498-0499, (2015/02/25)
The present invention is concerned with a novel process for the preparation of a compound of formula I and its hydrates The compounds of formula I and the corresponding hydrates are pharmaceutically active substances.
(3,4-DICHLORO-PHENYL)-((S)-3-PROPYL-PYRROLIDIN-3-YL)-METHANONE HYDROCHLORIDE AND MANUFACTURING PROCESSES
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Page/Page column 108, (2013/11/18)
The present invention is concerned with a novel process for the preparation of a compound of formula I and its hydrates, as well as with a crystall polymorph thereof. The compounds of formula (I) and the corresponding hydrates are pharmaceutically active substances.
An improved synthesis of 2-oxa-7-azaspiro[3,5]nonane and analogs as novel reagents in medicinal chemistry
Xu, Ruo,Czarniecki, Michael,Man, Jos De,Pan, Jianping,Qiang, Li,Root, Yuriko,Ying, Shihong,Su, Jing,Sun, Xijun,Zhang, Yuping,Yu, Tao,Zhang, Yang,Hu, Tao,Chen, Shu-Hui
scheme or table, p. 3266 - 3270 (2011/07/08)
A detailed synthesis of novel spirocyclic oxetane analogs is described for the first time.
