70441-03-1Relevant articles and documents
Design, Synthesis and Biological Investigation of Flavone Derivatives as Potential Multi-Receptor Atypical Antipsychotics
Chen, Yin,Gao, Lanchang,Hao, Chao,Jin, Jian,Liu, Bi-Feng,Liu, Xin,Ma, Ru,Xiong, Jiaying,Yang, Zhengge,Zhang, Guisen
, (2020/09/18)
The design of a series of novel flavone derivatives was synthesized as potential broad-spectrum antipsychotics by using multi-receptor affinity strategy between dopamine receptors and serotonin receptors. Among them, 7-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl) piperidin- 1-yl) butoxy)-2,2-dimethylchroman-4-one (6j) exhibited a promising preclinical profile. Compound 6j not only showed high affinity for dopamine D2, D3, and serotonin 5-HT1A, 5-HT2A receptors, but was also endowed with low to moderate activities on 5-HT2C, α1, and H1 receptors, indicating a low liability to induce side effects such as weight gain, orthostatic hypotension and QT prolongation. In vivo behavioral studies suggested that 6j has favorable effects in alleviating the schizophrenia-like symptoms without causing catalepsy. Taken together, compound 6j has the potential to be further developed as a novel atypical antipsychotic.
Synthesis, structure-activity relationship studies, and antibacterial evaluation of 4-chromanones and chalcones, as well as olympicin A and derivatives
Feng, Li,Maddox, Marcus M.,Alam, Md. Zahidul,Tsutsumi, Lissa S.,Narula, Gagandeep,Bruhn, David F.,Wu, Xiaoqian,Sandhaus, Shayna,Lee, Robin B.,Simmons, Charles J.,Tse-Dinh, Yuk-Ching,Hurdle, Julian G.,Lee, Richard E.,Sun, Dianqing
, p. 8398 - 8420 (2015/02/19)
On the basis of recently reported abyssinone II and olympicin A, a series of chemically modified flavonoid phytochemicals were synthesized and evaluated against Mycobacterium tuberculosis and a panel of Gram-positive and -negative bacterial pathogens. Some of the synthesized compounds exhibited good antibacterial activities against Gram-positive pathogens including methicillin resistant Staphylococcus aureus with minimum inhibitory concentration as low as 0.39 μg/mL. SAR analysis revealed that the 2-hydrophobic substituent and the 4-hydrogen bond donor/acceptor of the 4-chromanone scaffold together with the hydroxy groups at 5- and 7-positions enhanced antibacterial activities; the 2′,4′-dihydroxylated A ring and the lipophilic substituted B ring of chalcone derivatives were pharmacophoric elements for antibacterial activities. Mode of action studies performed on selected compounds revealed that they dissipated the bacterial membrane potential, resulting in the inhibition of macromolecular biosynthesis; further studies showed that selected compounds inhibited DNA topoisomerase IV, suggesting complex mechanisms of actions for compounds in this series.
Synthesis and antitubercular activity of amino alcohol fused spirochromone conjugates
Mujahid,Gonnade,Yogeeswari,Sriram,Muthukrishnan
supporting information, p. 1416 - 1419 (2013/03/14)
A series of 21 new amino alcohol fused spirochromone conjugates have been synthesized, characterized with analytical data and evaluated their antimycobacterial activity against Mycobacterium tuberculosis (virulent strain H37Rv) in vitro. Some of the compounds exerted significant inhibition, in particular, compound 4f found to be the most potent derivative exhibiting MIC = 3.13 μg/mL.
Discovery of novel benzopyranyl tetracycles that act as inhibitors of osteoclastogenesis induced by receptor activator of NF-κB ligand
Zhu, Mingyan,Kim, Myung Hee,Lee, Sanghee,Bae, Su Jung,Kim, Seong Hwan,Park, Seung Bum
supporting information; experimental part, p. 8760 - 8764 (2011/02/23)
A novel benzopyran-fused molecular framework 7ai was discovered as a specific inhibitor of RANKL-induced osteoclastogenesis using a cell-based TRAP activity assay from drug-like small-molecule libraries constructed by diversity-oriented synthesis. Its inhibitory activity was confirmed by in vitro evaluations including specific inhibition of RANKL-induced ERK phosphorylation and NF-κB transcriptional activation. 7ai can serve as a specific small-molecule modulator for mechanistic studies of RANKL-induced osteoclast differentiation as well as a potential lead for the development of antiresorptive drugs.
An excellent protocol for the synthesis of benzopyrans using basic resin under MWI
Tripathi,Koul,Taneja, Subhash C
experimental part, p. 1561 - 1564 (2011/02/22)
A convenient, microwave promoted novel protocol for the synthesis of diverse kinds of substituted benzopyrans from the corresponding variety of substituted hydroxy acetophenones and keto compounds using Amberlite IRA 400 resin (basic resin) under solvent-free conditions, has been developed. This protocol is mild and more efficient than the other reported methods.
Development of a benzopyran-containing androgen receptor antagonist to treat antiandrogen-resistant prostate cancer
Oh, Sangmi,Nam, Hye Jin,Park, Jongmin,Beak, Sung Hee,Park, Seung Bum
experimental part, p. 529 - 533 (2010/12/25)
Antagonizing cancer 2 000 druglike small molecules were screened and a scaffold identified as a potentially novel androgen receptor antagonist framework. A focused library of 19 derivatives was then synthesized and evaluated in vitro against LNCaP prostate cancer cell line. A novel compound (6 f) was identified as a promising lead compound for the further development of new therapeutic agents against hormone-refractory prostate cancer.
Microwave assisted facile and efficient synthesis of benzopyran
Tripathi,Koul,Taneja
experimental part, p. 301 - 304 (2009/12/03)
A convenient, fast and high yielding method for the preparation of 3,4-dihydrobenzopyrans has been achieved by the condensation of various acetophenones with different keto compounds in the presence of a base, assisted by microwave activation under solvent free conditions with or without use of a solid support.
COMPOUNDS WITH EMBEDDED BENZOPYRAN MOTIF FOR CORE STRUCTURES AND PREPARATION METHOD THEREOF
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Page/Page column 19, (2010/01/31)
The present invention relates to a compound having benzopyran core, a preparation method of the derivatives by liquid phase synthesis and solid phase synthesis through diversity-oriented synthesis, and an anticancer agent comprising the compound that exhi
COMPOUNDS WITH EMBEDDED BENZOPYRAN MOTIF FOR CORE STRUCTURES AND PREPARATION METHOD THEREOF
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Page/Page column 31, (2008/12/06)
The present invention relates to a compound having benzopyran core, a preparation method of the derivatives by liquid phase synthesis and solid phase synthesis through diversity-oriented synthesis, and an anticancer agent comprising the compound that exhi
Concise and diversity-oriented synthesis of novel scaffolds embedded with privileged benzopyran motif
Ko, Sung Kon,Jang, Hwan Jong,Kim, Eunha,Park, Seung Bum
, p. 2962 - 2964 (2008/09/19)
A branching DOS strategy for an unbiased natural product-like library with embedded privileged benzopyran motif was established to provide complexity and diversity of resulting heterocycles with desired drug-likeness. The importance of skeletal diversity
