- Synthesis of 4-ethyl-5-methyl-5,6-dihydrophenanthridine-8,9-diol as the key intermediate of potent agonists of the Wnt signalling pathway
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The synthesis of 4-ethyl-5-methyl-5,6-dihydro-phenanthridine-8,9-diol as the key intermediate of a series of potent Wnt signalling pathway agonists is reported. This synthesis features a consecutive aryl-aryl and N-aryl coupling, leading to 4-ethyl-5-meth
- Jing, Chen-Xu,Cai, Jie-Yun,Zhang, Yu,Chen, Duo-Zhi,Hao, Xiao-Jiang
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- Tandem copper catalyzed regioselectiveN-arylation-amidation: synthesis of angularly fused dihydroimidazoquinazolinones and the anticancer agent TIC10/ONC201
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Herein, we present a copper-catalyzed tandem reaction of 2-aminoimidazolines andortho-halo(hetero)aryl carboxylic acids that causes the regioselective formation of angularly fused tricyclic 1,2-dihydroimidazo[1,2-a]quinazolin-5(4H)-one derivatives. The reaction involved in the construction of the core six-membered pyrimidone moiety proceededviaregioselectiveN-arylation-condensation. The presented protocol been successfully applied to accomplish the total synthesis of TIC10/ONC201, which is an active angular isomer acting as a tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL): a sought after anticancer clinical agent.
- Honnanayakanavar, Jyoti M.,Nanubolu, Jagadeesh Babu,Suresh, Surisetti
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supporting information
p. 8497 - 8501
(2021/10/20)
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- THIOXANTHONE DERIVATIVES, COMPOSITION COMPRISING THE SAME AND PATTERN FORMING METHOD COMPRISING SAID COMPOSITION
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Latent photoinitiator compounds are described, as well as compositions containing such compounds and their uses in photoinitated methods for producing photoresist structures.
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- COMPOUND FOR TREATMENT OR PREVENTION OF OBESITY OR DISEASES RELATED TO OBESITY, AND APPLICATION THEREOF
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A compound for treatment or prevention of obesity or diseases related to obesity, and an application thereof. Specifically, provided are a compound as represented by formula I, or a pharmaceutically-acceptable salt thereof, and a pharmaceutical compositio
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Paragraph 0271
(2020/08/09)
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- METHOD FOR PRODUCING 2-HALOGENATED BENZOIC ACIDS
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The purpose of the present invention is to provide a method for producing 2-halogenated benzoic acids, the method imparting high regioselectivity (high selectivity) and having a shorter reaction time than does the conventional reaction. This method for producing 2-halogenated benzoic acids, in order to achieve the above purpose, is characterized in that benzoic acids and a halogenating agent are reacted in the presence of an alkaline compound, making it possible to highly selectively obtain 2-halogenated benzoic acids.
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Paragraph 0061; 0062; 0067; 0068-0073
(2018/04/20)
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- Urolithin C, a gut metabolite of ellagic acid, induces apoptosis in PC12 cells through a mitochondria-mediated pathway
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Urolithins (Uros), metabolites of ellagitannins (ET) and ellagic acid (EA) produced by gut microbiota, showed better bioavailability and extensive bioactivity, and were considered as the active compounds responsible for the health benefits exerted by ET-containing foodstuffs. Here, we chemically synthesized three Uros including Uros A, B, and C and compared their anti-proliferative activities with that of EA in PC12 cells. MTT assay showed that EA significantly promoted, while Uros significantly inhibited the proliferation of PC12 cells, among which UroC showed the strongest anti-proliferation. UroC treatment actively increased the lactate dehydrogenase (LDH) release and lipid peroxidation malondialdehyde (MDA), stimulated reactive oxygen species (ROS) formation and mitochondrial membrane depolarization, and caused calcium dyshomeostasis. Furthermore, flow cytometry analysis showed that UroC treatment induced apoptosis and S phase cell cycle arrest with increasing UroC concentrations. Consequently, UroC also induced imbalance in the Bcl-2/Bax ratio, which triggered the caspase cascade, thereby shifting the balance in favor of apoptosis, as evidenced by western blotting and real-time PCR. These observations indicated that UroC possessed significantly different anti-proliferation activities from EA, and actively induced cell apoptosis through a mitochondria-mediated pathway.
- Yin, Peipei,Zhang, Jianwei,Yan, Linlin,Yang, Lingguang,Sun, Liwei,Shi, Lingling,Ma, Chao,Liu, Yujun
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p. 17254 - 17263
(2017/03/27)
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- Phenanthridine Derivatives, Preparation Methods and Uses Thereof
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The present invention relates to the pharmaceutical field, in particular to a phenanthridine derivative as shown in general formula (1) a pharmaceutical composition comprising the derivative, its preparation method, and its uses in manufacture of a medica
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Paragraph 0125
(2016/04/19)
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- Efficient and convenient copper-free Pd(OAc)2/Ruphos-catalyzed Sonogashira coupling in the preparation of corfin analogues
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The Sonogashira coupling reaction of 3-chloro-1H-isochromen-1-one and terminal alkynes, in the presence of catalytic system-Pd(OAc)2/Ruphos, Et3N base, and tetrahydrofuran solvent under aqueous conditions, provided novel 3-(alkynyl)-
- Dasaradhan, Changalaraya,Kumar, Yadavalli Suneel,Prabakaran, Kamalakannan,Khan, Fazlur-Rahman Nawaz,Jeong, Euh Duck,Chung, Eun Hyuk
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supporting information
p. 784 - 788
(2015/01/30)
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- Palladium catalyzed Suzuki Miyaura cross coupling of 3-chloroisochromen-1-one: Synthesis of glomellin and reticulol analogues
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A facile protocol has been developed for a series of 3-substituted isochromen-1-ones utilizing Suzuki coupling strategy. The reaction of 3-chloroisochromen-1one, 1 with different boronic acids utilizing PdCl2(PPh3)2-Ruphos catalytic system gave diversified 3-substituted isochromen-1-ones in excellent yields. The methodology has been utilized in the synthesis of glomellin and reticulol analogues.
- Kumar, Yadavalli Suneel,Dasaradhan, Changalaraya,Prabakaran, Kamalakannan,Manivel, Pitchai,Nawaz Khan, Fazlur-Rahman,Jeong, Euh Duck,Chung, Eun Hyuk
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supporting information
p. 941 - 945
(2015/02/05)
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- Efficient copper-free Pd(OAc)2/Ruphos-catalyzed Sonogashira coupling in the preparation of 3′-hydroxycorfin and gymnopalynes A analogues
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An efficient method involving copper-free Pd(OAc)2/Ruphos-catalyzed Sonogashira coupling strategy for a variety of 3-alkynyl isochromen-1-ones has been developed. Sonogashira coupling in the presence of catalytic system - Pd(OAc)2/Ruphos, Et3N base, and tetrahydrofuran solvent under aqueous and room temperature conditions, provided novel 3-(alkynyl)-1H-isochromen-1-ones in excellent yields. The methodology has also been extended toward natural isochromen-1-one-3′-hydroxycorfin and gymnopalynes A analogues.
- Dasaradhan, Changalaraya,Suneel Kumar, Yadavalli,Nawaz Khan, Fazlur-Rahman,Jeong, Euh Duck,Chung, Eun Hyuk
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supporting information
p. 187 - 191
(2015/02/19)
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- Iodine-promoted oxidative conversion of o-vinyl diaryl ketones into o-acetyl diaryl ketones, synthesis of 1-methyl-4-arylphthalazines as analogues of podophyllotoxin
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A new method is described for the metal-free oxidation of o-vinyl diaryl ketones in the presence of molecular iodine or N-iodosuccinimide to give o-acetyl diaryl ketones. This transformation involves the initial formation of an iodohydrin, and the o-carbo
- Harikrishna, Kommidi,Mukkamala, Ramesh,Hinkelmann, Bettina,Sasse, Florenz,Aidhen, Indrapal Singh
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p. 1066 - 1075
(2014/03/21)
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- Iodine-promoted oxidative conversion of o-vinyl diaryl ketones into o-acetyl diaryl ketones, synthesis of 1-methyl-4-arylphthalazines as analogues of podophyllotoxin
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A new method is described for the metal-free oxidation of o-vinyl diaryl ketones in the presence of molecular iodine or N-iodosuccinimide to give o-acetyl diaryl ketones. This transformation involves the initial formation of an iodohydrin, and the o-carbo
- Harikrishna, Kommidi,Mukkamala, Ramesh,Hinkelmann, Bettina,Sasse, Florenz,Aidhen, Indrapal Singh
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p. 1066 - 1075
(2015/10/05)
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- METHOD FOR PRODUCING 2-BROMO-4,5-DIALKOXY BENZOIC ACID
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Provided is a method for effectively producing a 4,5-dialkoxy-2-hydroxybenzoic acid from an inexpensive raw material. A method for producing a 2-bromo-4,5-dialkoxybenzoic acid represented by the following formula (2): (wherein each of R1 and R2 represents a lower alkyl group), the method including causing a 3,4-dialkoxybenzoic acid represented by the following formula (1): (wherein R1 and R2 have the same meanings as defined above) to react with bromine in concentrated hydrochloric acid.
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Paragraph 0028; 0029
(2013/10/07)
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- Design, synthesis, and biological evaluation of bromophenol derivatives as protein tyrosine phosphatase 1B inhibitors
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3-Bromo-4,5-bis(2,3-dibromo-4,5-dihydroxybenzyl)-1,2-benzenediol (BDB) is a bromophenol purified from the marine red alga Rhodomela confervoides and exhibits potent protein tyrosine phosphatase 1B (PTP1B) inhibition (IC 50 = 1.7 μmol/L). In an effort to improve the PTP1B inhibitory activity, a series of derivatives were designed, synthesized, and evaluated in vitro. The preliminary structure-activity relationship indicated that the tricyclic scaffold and multi-bromine atoms (four to five) attached to the aryl rings are important for PTP1B inhibition. Among these, compound 26 exhibited remarkable inhibitory activity against PTP1B with an IC50 of 0.89 μmol/L, which was approximately two-fold more potent than the initial lead compound BDB.
- Jiang, Bo,Shi, Dayong,Cui, Yongchao,Guo, Shuju
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experimental part
p. 444 - 453
(2012/08/27)
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- PHOSPHODIESTERASE 10 INHIBITORS
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The present invention if directed to certain cinnoline compounds that are PDE10 inhibitors, pharmaceutical compositions containing such compounds and processes for preparing such compounds. The invention is also directed to methods of treating diseases mediated by PDE10 enzyme, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.
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Page/Page column 62
(2008/06/13)
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- Discotic liquid crystals through molecular self-assembly
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We have created self-assembled disk-like aggregates of predictable stoichiometry which form discotic liquid crystalline phases. Attempts to assemble multiple molecules of one compound radially about a second acting as a template failed, presumably owing t
- Kleppinger, Ralf,Lillya, C. Peter,Yang, Changqing
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p. 4097 - 4102
(2007/10/03)
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- Oxygenated phenanthrenes via quinol ketals: Cyclization vs. migration
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2-methoxyphenanthrenes were prepared by reaction of lithiated 2-bromostyrenes with quinone monoketals followed by acid-mediated cyclization of the resulting p-arylquinol ketals. Substitution at the bromostyrene side-chain or the quinone monoketal ring had only a modest effect on yields, but oxygen substitution on the bromostyrene aromatic nucleus resulted in a competing 1,2-aryl migration arising during the quinol ketal cyclization step. The extent of this rearrangement was found to be a function of the Lewis acid/solvent system employed.
- Morrow, Gary W.,Marks, Tina M.,Sear, Debra L.
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p. 10115 - 10124
(2007/10/02)
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- SYNTHESIS OF FAGARONINE
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Alkaloids fagaronine (I), dihydrofagaronine (XXV) and oxyfagaronine (XXVI) were synthesized from 2,3-dihydroxynaphthalene (II) and 2-bromo-4,5-dimethoxybenzaldehyde (XI), the key synthetic steps being the preparation of 2-hydroxy-3-methoxy-5-nitronaphthal
- Smidrkal, Jan
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p. 3184 - 3192
(2007/10/02)
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