Design, synthesis, and testing of an isoquinoline-3-carboxylic-based novel anti-tumor lead

Gao, Fei; Liu, Haiqing; Li, Li; Guo, Jianpeng; Wang, Yuji; Zhao, Ming; Peng, Shiqi

doi:10.1016/j.bmcl.2015.09.014

Cited by 12 publications

(8 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The therapeutic potential of 6 in vivo was evaluated using the S180 tumor-bearing mouse model . Twenty-four hours after implantation, the mice were randomized into groups of 5 with 10 mice in each group.…”

Section: Results and Discussionmentioning

confidence: 99%

“…As DNA intercalators, their planar aromatic moieties insert between adjacent base pairs, which decreases the DNA helical twist and length of the DNA strand, and disrupts important processes such as DNA replication, transcription, and repair . Recently, many DNA intercalators have been used as potential lead compounds due to their inhibitory effect on the growth of cancer cells. , Besides, bivalent ligands formed by the tethering of two DNA intercalating agents by an appropriately designed spacer have proved more effective inhibitors than their corresponding monomers by increasing the number of binding sites and improving the interaction of ligands with their corresponding receptors. − We recently reported that a bivalent ligand based on isoquinoline-3-carboxylic acid exhibited improved antitumor activity compared to isoquinoline-3-carboxylic acid alone …”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Design and Synthesis of Biotinylated Bivalent Carboline Derivatives as Potent Antitumor Agents

et al. 2020

Self Cite

View full text Add to dashboard Cite

Compound 6, a novel β-carboline comprising two 1-methyl-9H-βcarboline-3-carboxylic acids and a biotin moiety conjugated together using tris(2aminoethyl)amine, was synthesized and tested for its cytotoxicity toward MCF-7 and HepG2 cell lines and antitumor potency in an S180 tumor-bearing mouse model. Compound 6 was delivered via biotin receptor-mediated endocytosis and exerted its therapeutic effects by intercalation binding with DNA. In vivo antitumor evaluations of 6 revealed that it is efficacious and exhibits low systemic toxicity.

show abstract

Section: Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Biotinylated Bivalent Carboline Derivatives as Potent Antitumor Agents

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

“…Among a variety of bases evaluated, inorganic bases generally facilitated the transformation, and the organic base DIPEA (N,N-diisopropylethylamine) showed the best efficiency. In contrast, the yield became very poor when DBU was present (entries [11][12][13][14]. Next, common solvents, such as THF, DMF, and 1,2-dichloroethane, were screened.…”

Section: Resultsmentioning

confidence: 99%

“…Due to their unique DNA binding properties, isoquinolines and their derivatives show a wide range of biological activities, such as in vasodilatation [5][6][7], as well as for its antibacterial [3,8,9], anti-malarial [10], anti-HIV [11,12] and anti-tumor properties [13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Isoquinolinones via Regioselective Palladium-Catalyzed C–H Activation/Annulation

Han

et al. 2017

Catalysts

View full text Add to dashboard Cite

Abstract:The isoquinoline motif and its derivatives are of significant interest due to their important biological activities. The effective synthesis of substituted isoquinoline compounds has historically been a significant challenge. A new palladium-catalyzed C-H activation/annulation of N-methoxy benzamides and 2,3-allenoic acid esters is described. For the first time, 2,3-allenoic acid esters are employed for the syntheses of 3,4-substituted hydroisoquinolones, the heteroannulation of allenes proceeded smoothly and afforded the products with good yields and excellent regioselectivity.

show abstract

“…4.3 芳烃 C(sp 2 )-H 与醛 C(sp 2 )-H 的 CDC 反应醛氢具有一定酸性, 在适当条件下也可与芳烃直接发生 CDC 反应, 实现活性芳酰衍生物 [127][128][129][130] 的直接构建. 2013 年, Antonchick 课题组 [131] 利用高价碘化合物 PhI(OCOCF 3 ) 2 作为氧化剂 , 在叠氮基三甲基硅烷 (TMSN 3 )的促进下实现了氮杂环芳烃与醛的 CDC 反应 (Scheme 44, a).…”

Section: C(sp 3 )-C(sp )偶联反应unclassified

Alternative Strategies Enabling Cross-Dehydrogenative Coupling: Access to C—C Bonds

Wang¹,

Ying²,

Yu³

et al. 2021

Chinese Journal of Organic Chemistry

View full text Add to dashboard Cite

Cross-dehydrogenative coupling (CDC) reactions have been esteemed as one of the straightforward and efficient tool for C-C bond formation. Typically, these reactions are generally realized via solvent-based thermochemistry, using a round bottom flask and a magnetic or mechanical stirrer. With the development of new synthetic strategies, alternative technologies currently available in laboratories that facilitate CDC reactions, such as photochemistry, electrochemistry and mechanochemistry have arisen rapidly, providing green and high efficiency strategies for the construction of C-C bonds which are perfect complement to traditional thermochemistry. In order to compare the advantages of each approaches more clearly, and promote the development of CDC reactions, CDC reactions related to two or more enabling technologies of same or similar substrates are reviewed, hoping to provide help for the development of CDC reaction and the development of new organic synthesis methods.

show abstract

Design, synthesis, and testing of an isoquinoline-3-carboxylic-based novel anti-tumor lead

Cited by 12 publications

References 25 publications

Design and Synthesis of Biotinylated Bivalent Carboline Derivatives as Potent Antitumor Agents

Design and Synthesis of Biotinylated Bivalent Carboline Derivatives as Potent Antitumor Agents

Synthesis of Isoquinolinones via Regioselective Palladium-Catalyzed C–H Activation/Annulation

Alternative Strategies Enabling Cross-Dehydrogenative Coupling: Access to C—C Bonds

Contact Info

Product

Resources

About