- Synthesis of 3-Ferrocenyl Isocoumarins
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The derivatives of 3-ferrocenyl isocoumarin were synthesized by the condensation of substituted homothphalic anhydride with ferrocene using phosphoric acid or anhydrous aluminium chloride as cyclising agent. Substituted homophthalic acid did not condense with ferrocene so homophthalic acids were converted into their anhydride and then allowed to react with ferrocene in the presence of polyphosphoric acid or in the presence of anhydrous aluminium chloride using dichloromethane as the solvent to give 3-ferrocenyl isocoumarins. 7-Methoxy, 6-methyl, 5,7-dihydroxy, 6,7-dimethoxy and 5,7-dimethoxy derivatives of 3-ferrocenyl isocoumarin were synthesized. All the compounds were characterised by melting point determination, elemental and spectral analysis.
- Sinha, Neeta
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p. 976 - 979
(2020/11/25)
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- Amide-like derivative impurity and application thereof
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The invention relates to an amide-like derivative impurity and application thereof. The invention belongs to the field of medical chemistry, and particularly relates to an impurity A, an impurity B, an impurity G, a preparation method thereof, and applica
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Paragraph 0125-0126; 0128
(2020/07/12)
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- Sulfones as Synthetic Linchpins: Transition-Metal-Free sp3–sp2 and sp2–sp2 Cross-Couplings Between Geminal Bis(sulfones) and Organolithium Compounds
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A valuable umpolung strategy that highlights the ambiphilic nature of the bis(phenylsulfonyl)methyl synthon and demonstrates its utility as a synthetic linchpin is reported. Although the bis(phenylsulfonyl)methyl group is typically introduced as an sp3-carbon nucleophile, it is demonstrated that it can also function as an effective sp2-carbon electrophile in the presence of organolithium nucleophiles. Alkyl- and aryllithiums couple with the central carbon of the bis(phenylsulfonyl)methyl unit to ultimately generate trisubstituted alkenes, comprising formal sp3–sp2 and sp2–sp2 cross-couplings between organolithium reagents and bis(sulfones). This process occurs almost instantaneously at ?78 °C in the absence of any transition metals. By developing this curious transformation, it has been demonstrated that bis(phenylsulfonyl)methane is a valuable synthetic linchpin, which can undergo two C?C bond-forming processes as an sp3-nucleophile, followed by a third C?C bond-forming reaction as an effective sp2-electrophile. This discovery significantly enhances the utility of this ubiquitous, but underutilized, linker group.
- Trost, Barry M.,Kalnmals, Christopher A.
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supporting information
p. 9066 - 9074
(2018/06/29)
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- Design, synthesis and evaluation of 6-aryl-indenoisoquinolone derivatives dual targeting ERα and VEGFR-2 as anti-breast cancer agents
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The estrogen receptors have played important roles in breast cancer development and progression. Selective estrogen receptor modulators, such as Tamoxifen, have showed great benefits in the treatment and prevention of breast cancer. But the disadvantages of induction of endometrial cancer and drug resistance have limited their use. Multiple ligand which act at multiple biomolecular targets may exert favorable advantages of improved efficacy with lower incidence of side effects. In this work, we described the synthesis and evaluation of a series of 6-aryl-indenoisoquinolone derivatives as dual ERα and VEGFR-2 inhibitors. These compounds presented good ERα binding affinity and ERα antagonistic activity, as well as potent VEGFR-2 inhibitory potency. They also possessed excellent anti-proliferative activities against MCF-7, MDA-MB-231, Ishikawa and HUVEC cell lines. Further investigation of selective compound 21c showed that it was able to inhibit the activation of VEGFR-2 and the signaling transduction of Raf-1/MAPK/ERK pathway in MCF-7 cells.
- Tang, Zhichao,Wu, Chengzhe,Wang, Tianlin,Lao, Kejing,Wang, Yejun,Liu, Linyi,Muyaba, Moses,Xu, Pei,He, Conghui,Luo, Guoshun,Qian, Zhouyang,Niu, Shaoxiong,Wang, Lijun,Wang, Ying,Xiao, Hong,You, Qidong,Xiang, Hua
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p. 328 - 339
(2016/06/01)
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- Design, synthesis and biological evaluation of 3-substituted indenoisoquinoline derivatives as topoisomerase I inhibitors
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A new series of indenoisoquinoline derivatives was designed and synthesized. The in vitro anti-proliferative activity of these novel compounds was evaluated in HepG2, A549 and HCT-116 cell lines. Compounds 9a, 9b, 10a, 10c, 10e, 18a and 18b manifested potent inhibitory activity against the three tested cancer cell lines. Nineteen compounds were also tested for Top I inhibition at 50 μM. Almost all the tested compounds showed potent Top I inhibition activity at this concentration. The most potent compounds 9a and 10a demonstrated more cytotoxicity than HCPT and TPT and was comparable to CPT in inhibitory activities on Top I in our biological assay.
- Zhao, Qian,Xu, Xi,Xie, Zhouling,Liu, Xiao,You, Qidong,Guo, Qinglong,Zhong, Yi,Li, Zhiyu
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p. 1068 - 1072
(2016/05/24)
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- 3-PHENYL-7-HYDROXY-ISOCOUMARINS AS MACROPHAGE MIGRATION INHIBITORY FACTOR (MIF) INHIBITORS
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This invention relates to 3-phenyl-7-hydroxy-isocoumarin compounds which are MIF inhibitors, compositions comprising said inhibitors and methods for treating or preventing diseases associated with MIF.
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Page/Page column 36
(2016/01/21)
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- Synthesis and biological evaluation of 2,3-diaryl isoquinolinone derivatives as anti-breast cancer agents targeting ERα and VEGFR-2
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The estrogen receptor α is recognized as important pharmaceutical target for breast cancer therapy, and vascular endothelial growth factor receptors (VEGFRs) play important roles in tumor angiogenesis including breast cancer. A series of 2,3-diaryl isoqui
- Tang, Zhichao,Niu, Shaoxiong,Liu, Fei,Lao, Kejing,Miao, Jingshan,Ji, Jinzi,Wang, Xiang,Yan, Ming,Zhang, Luyong,You, Qidong,Xiao, Hong,Xiang, Hua
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supporting information
p. 2129 - 2133
(2014/05/06)
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- Enantioselective organic anhydride reactions
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Disclosed herein is enantioselective synthetic method comprising reacting an enolisable C4-C50 organic anhydride with a second compound selected from the group consisting of an aldehyde, a ketone, an aldimine, a ketimine or a Michael Acceptor in the presence of a bifunctional organocatalyst. The reaction may find particular utility in the enantioselective synthesis of medicinally relevant heterocycles, such as dihydroisocoumarins and dihydroisoquinolinones.
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Paragraph 0076
(2013/09/26)
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- NOVEL INHIBITOR COMPOUNDS OF PHOSPHODIESTERASE TYPE 10A
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The present invention relates to compounds which are inhibitors of phosphodiesterase type 10A and to their use for the manufacture of a medicament and which thus are suitable for treating or controlling of medical disorders selected from neurological diso
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Paragraph 0989; 0990
(2013/05/21)
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- ENANTIOSELECTIVE ORGANIC ANHYDRIDE REACTIONS
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Disclosed herein is enantioselective synthetic method comprising reacting an enolisable C4-C50 organic anhydride with a second compound selected from the group consisting of an aldehyde, a ketone, an aldimine, a ketimine or a Michael Acceptor in the presence of a bifunctional organocatalyst. The reaction may find particular utility in the enantioselective synthesis of medicinally relevant heterocycles, such as dihydroisocoumarins and dihydroisoquinolinones.
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Page/Page column
(2013/09/26)
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- A catalytic asymmetric reaction involving enolizable anhydrides
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In the presence of a highly efficient novel bifunctional organocatalyst at low loadings under mild conditions, enolizable homophthalic anhydrides can be added to a range of aromatic and aliphatic aldehydes to give dihydroisocoumarins, with excellent yields and diastereo-and enantiocontrol (up to 99% ee).
- Cornaggia, Claudio,Manoni, Francesco,Torrente, Esther,Tallon, Sean,Connon, Stephen J.
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supporting information; experimental part
p. 1850 - 1853
(2012/06/16)
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- A short and efficient construction of the dibenzo[c,h]chromen-6-one skeleton
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We hereby report a major revision of the synthetic methodology for construction of the dibenzochromenone skeleton. Homophthalic acid derivatives were reacted with thionylchloride/DMF in the presence of NaN 3. As the main product, dibenzochromen
- Delioemeroglu, Murat K.,Oezcan, Sevil,Balcia, Metin
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scheme or table
p. 148 - 160
(2010/08/04)
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- NOVEL INHIBITORS OF FLAVIVIRUS REPLICATION
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The present invention relates to a series of novel compounds, methods to prevent or treat viral infections by using the novel compounds, processes for preparation of the compounds, their use to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections, particularly infections with viruses belonging to the family of the Flaviviridae and more preferably infections with Hepatitis C virus (HCV). The present invention also relates to the novel compounds for use as a medicine, more preferably for use as a medicine for the prevention or treatment of viral infections, preferably infections with viruses belonging to the family of the Flaviviridae.
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Page/Page column 135
(2010/06/15)
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- Hydroxyl-Substituted sulfonylureas as potent inhibitors of specific [3H]Glyburide binding to rat brain synaptosomes
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We are seeking to discover potent CNS-active sulfonylureas with structural features that allow for the formation of several types of prodrugs. We report herein the syntheses of compounds comprising an initial series of hydroxyl-substituted analogues of the potent ATP-sensitive potassium channel blockers glyburide (glibenclamide) and gliquidone. Somewhat unexpectedly, several of the compounds were found to be comparably potent to glyburide as inhibitors of specific [3H]glyburide binding in rat brain preparations.
- Hill, Ronald A.,Rudra, Sonali,Peng, Bo,Roane, David S.,Bounds, Jeffrey K.,Zhang, Yang,Adloo, Ahmad,Lu, Tiansheng
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p. 2099 - 2113
(2007/10/03)
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