54903-50-3Relevant academic research and scientific papers
Light-Driven Intramolecular C?N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex
Jing, Dong,Lu, Cong,Chen, Zhuo,Jin, Songyang,Xie, Lijuan,Meng, Ziyi,Su, Zhishan,Zheng, Ke
supporting information, p. 14666 - 14672 (2019/09/06)
Reported herein is a visible-light-driven intramolecular C?N cross-coupling reaction under mild reaction conditions (metal- and photocatalyst-free, at room temperature) via a long-lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N-substituted polycyclic quinazolinone derivatives with a broad substrate scope (>50 examples) and further exploited to synthesize the natural products tryptanthrin, rutaecarpine, and their analogues. The success of gram-scale synthesis and solar-driven transformation, as well as promising tumor-suppressing biological activity, proves the potential of this strategy for practical applications. Mechanistic investigations, including control experiments, DFT calculations, UV-vis spectroscopy, EPR, and X-ray single-crystal structure of the key intermediate, provides insight into the mechanism.
Long pepper amide analogs, preparation method and application thereof
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Paragraph 0057; 0058, (2017/08/25)
The invention relates to the pharmaceutical chemistry field, and concretely relates to a piplartine analogue (I) or (II), a preparation method therefor and pharmaceutical compositions containing the piplartine analogue (I) and (II). The pharmacodynamic experiments prove that piplartine analogue can be used for treating or preventing thromboembolism diseases. The structural formulas of the piplartine analogue (I) and (II) are shown in the specification.
A method for preparing pyridine [...] of hydrochloric acid
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Paragraph 0060-0062, (2018/02/04)
The invention discloses a preparation method of ticlopidine hydrochloride. The preparation method comprises the following steps: A, adding a certain amount of reactive raw materials into a reaction container, and carrying out reaction at the temperature of 30-80 DEG C for 1-10 hours, wherein the raw materials include 2-thiophene ethylamine, methanal, a haloalkane solvent and a solid super acidic catalyst; B, cooling the solution of reaction to room temperature; C, adding a certain amount of a solid alkaline catalyst and 2-chlorobenzyl chloride into the solution of reaction, carrying out reaction at the temperature of 30-80 DEG C for 1-10 hours, stopping heating, and standing to precipitate; D, filtering to obtain a filtrate; and E, introducing hydrogen chloride into the filtrate to obtain ticlopidine hydrochloride. The solid super acidic catalyst and the solid alkaline catalyst are adopted by the preparation method, and the heterogeneous tandem reaction is carried out. The technology has the advantage of convenience in post-treatment, is easy to operate, can not cause corrosion to equipment and is economical, practical and environment-friendly, less three wastes are produced, and the solid acid and alkali can be reused.
Reductive iodonio-Claisen rearrangement of iodothiophene diacetates with allylsilanes: Formal synthesis of Plavix
Nguyen, Hai,Khatri, Hem Raj,Zhu, Jianglong
supporting information, p. 5464 - 5466 (2013/09/23)
Iodothiophene diacetates react with allyltrimethylsilanes in the presence of boron trifluoride diethyl etherate to afford corresponding ortho-allyliodothiophenes via reductive iodonio-Claisen rearrangement. This method has been successfully applied to the synthesis of Plavix, a blood clot inhibitor used to reduce the risk of heart attack and stroke.
An efficient and convenient synthesis of 4,5,6,7-tetrahydrothieno[3,2-c] pyridines by a modified Pictet-Spengler reaction via a formyliminium ion intermediate
Kitabatake, Michikazu,Hashimoto, Aki,Saitoh, Toshiaki,Sano, Takehiro,Mohri, Kunihiko,Horiguchi, Yoshie
experimental part, p. 1903 - 1921 (2011/04/12)
A synthesis of N-formyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridines (5) was achieved in a highly efficient manner via trifluoroacetic acid catalyzed cyclization of formyliminium ion (4), which was produced by imination of 2-(2-thienyl)ethylamine (1) and a carbonyl compound (2) using titanium(IV) tetraisopropoxide followed by formylation with acetic-formic anhydride in a one-pot procedure. This modified Pictet-Spengler reaction provides a convenient method for preparing 4,5,6,7-tetahydrothieno[3,2-c]pyridines (6) possessing various substituents at C-4. The Japan Institute of Heterocyclic Chemistry.
PROCESS FOR THE PREPARATION OF CLOPIDOGREL BISULPHATE FORM I
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Page/Page column 10, (2009/07/25)
The invention relates to a process for the preparation of crystalline form-I of S- (+)-clopidogrel bisulphate.
Highly selective copper-catalyzed ring expansion of vinyl thiiranes: Application to synthesis of biotin and the heterocyclic core of plavix
Rogers, Erik,Araki, Hiroshi,Batory, Lindsay A.,McInnis, Christine E.,Njardarson, Jon T.
, p. 2768 - 2769 (2007/10/03)
We report herein a new, highly selective, mild copper-catalyzed vinyl thiirane ring-expansion protocol for the formation of 2,5-dihydrothiophenes. Preliminary substrate scope and applications of this new synthetic disconnection to the formal racemic total synthesis of biotin and the synthesis of the antiplatelet blockbuster pharmaceutical agent Plavix are described. Copyright
11-BETA-HYDROXYSTEROID DEHYDROGENASE INHIBITORS
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Page/Page column 118, (2008/06/13)
There is provided a compound having Formula (I ) R1-Z-R2 wherein R1 is a group selected from optionally substituted fused polycyclic groups, substituted alkyl groups, branched alkyl groups, and optionally substituted cycioalkyl groups Z is a linker which is or comprises a carbonyl group or a isostere of a carbonyl group R2 is selected from optionally substituted aromatic rings and optionally substituted heterocyclic rings wherein (a) R2 is a 2-substituted thiophene group, and/or (b) Z is a group of the formula -C(=O)-CR3R4-X-(CR5R6)n-, wherein X is selected from NR7, S, O, S=O, and S(=O)2, wherein n is 0 or 1 and/or (c) R1 is an adamantyl group and Z is or comprises an amide group, and/or (d) R1 is an adamantyl group and Z is or comprises a group of the formula -(CR8R9)p- NR10-S(=O)2-(CR11R12)q-, wherein p is 0 or 1 and q is 0 or 1 and/or (e) R1 is an adamantyl group and Z is or comprises a group of the formula -(CR13R14)V-Y- (CR15R16)W- where Y is a heteroaryl group in which a bond in the heteroaryl ring is a isostere of a carbonyl group, wherein v is o or 1 and w is 0 or 1 ; wherein each of R3, R4, R5, R6, R8, R9, R11, R12, R13, R14, R15 and R16, are independently selected from H, hydrocarbyl and halogen, wherein each of R7 and R10 are independently selected from H and hydrocarbyl.
BISSULFONAMIDE COMPOUNDS AS AGONISTS OF GALR1, COMPOSITIONS, AND METHODS OF USE
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Page/Page column 74, (2008/06/13)
Embodiments of the present invention provide bissulfonamide compounds that are agonists of GalR1. The present invention further provides compositions comprising bissulfonamide compounds that are agonists of GalR1, and methods of use of such compounds and compositions.
Quinoline and naphthyridine carboxylic acid antibacterials
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, (2008/06/13)
Compounds having formula (I) or pharmaceutically acceptable salts or prodrugs thereof, are useful as antibacterial agents.
