Design, synthesis, and biological evaluation of novel tetrahydroisoquinoline derivatives as potential antitumor candidate

Zhu, Panhu; Ye, Wenfeng; Li, Jiaming; Zhang, Yanchun; Huang, Weijun; Cheng, Mohan; Wang, Yujun; Zhang, Yang; Liu, Huicai; Zuo, Jian

doi:10.1111/cbdd.12873

Cited by 17 publications

(12 citation statements)

References 25 publications

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“…The focus of patented inventions related to breast cancer was primarily on the development of novel pharmaceutical drugs, biological products, and devices for diagnosis and treatment. Chemical agents or functional groups such as “phenyl” (1995-2017) [54], “pyrazolo” (1995-2003) [55], “thieno” (2008-2013) [56], and “tetrahydroisoquinolines” (2017) [57] were most mentioned in the top 10 topic words and were reported to have antitumor effects in different years. In addition, “antibodies,” “binding,” “base sequence,” “polypeptides,” and “amino acid sequence” were the most frequent keywords of breast cancer mentioned in patents related to antibody therapy [58] and genetic diagnosis and treatment [59,60].…”

Section: Resultsmentioning

confidence: 99%

Technological Innovations in Disease Management: Text Mining US Patent Data From 1995 to 2017

Huang¹,

Zolnoori²,

Balls-Berry³

et al. 2019

J Med Internet Res

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Background Patents are important intellectual property protecting technological innovations that inspire efficient research and development in biomedicine. The number of awarded patents serves as an important indicator of economic growth and technological innovation. Researchers have mined patents to characterize the focuses and trends of technological innovations in many fields. Objective To expand patent mining to biomedicine and facilitate future resource allocation in biomedical research for the United States, we analyzed US patent documents to determine the focuses and trends of protected technological innovations across the entire disease landscape. Methods We analyzed more than 5 million US patent documents between 1995 and 2017, using summary statistics and dynamic topic modeling. More specifically, we investigated the disease coverage and latent topics in patent documents over time. We also incorporated the patent data into the calculation of our recently developed Research Opportunity Index (ROI) and Public Health Index (PHI), to recalibrate the resource allocation in biomedical research. Results Our analysis showed that protected technological innovations have been primarily focused on socioeconomically critical diseases such as “other cancers” (malignant neoplasm of head, face, neck, abdomen, pelvis, or limb; disseminated malignant neoplasm; Merkel cell carcinoma; and malignant neoplasm, malignant carcinoid tumors, neuroendocrine tumor, and carcinoma in situ of an unspecified site), diabetes mellitus, and obesity. The United States has significantly improved resource allocation to biomedical research and development over the past 17 years, as illustrated by the decreasing PHI. Diseases with positive ROI, such as ankle and foot fracture, indicate potential research opportunities for the future. Development of novel chemical or biological drugs and electrical devices for diagnosis and disease management is the dominating topic in patented inventions. Conclusions This multifaceted analysis of patent documents provides a deep understanding of the focuses and trends of technological innovations in disease management in patents. Our findings offer insights into future research and innovation opportunities and provide actionable information to facilitate policy makers, payers, and investors to make better evidence-based decisions regarding resource allocation in biomedicine.

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Section: Resultsmentioning

confidence: 99%

Technological Innovations in Disease Management: Text Mining US Patent Data From 1995 to 2017

Huang¹,

Zolnoori²,

Balls-Berry³

et al. 2019

J Med Internet Res

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“…The nitrogen containing heterocycles are very important precursors in the pharmaceutical and agrochemicals synthesis . The substituted tetrahydroisoquinolines have a broad range of biological activities, including antitumor and antimicrobial action .…”

Section: Introductionmentioning

confidence: 99%

A Facile One‐Pot Synthesis of 1,2,3,4‐Tetrahydroisoquinoline‐1‐carbonitriles via the Electrogenerated Cyanide Anions from Acetonitrile

et al. 2020

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The electrosynthesis of 1,2,3,4-tetrahydroisoquinoline-1-carbonitriles by acetonitrile reduction is a green and safe strategy to replace the traditional cyanation. Herein, we have obtained the 1,2,3,4-tetrahydroisoquinoline-1-carbonitrile in good yields by a simple reaction between dihydroisoquinolin-2-ium iodide and the electrogenerated acetonitrile formed under low temperature conditions, when a solution of dry acetonitrile is electrolyzed at a Carbon rod as cathode and a magnesium plate as anode in undivided cell. ChemistrySelectCommunications

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“…Numerous methodologies have been reported for the syntheses of THIQ analogs . In particular, THIQs substituted at the C1 and N positions display various biological activities, such as antitumor, anti‐HIV, antibacterial, and neuroprotective . For instance, solifenacin is an approved drug as a selective muscarinic M3 receptor antagonist for the treatment of overactive bladder (Figure ) .…”

Section: Introductionmentioning

confidence: 99%

Succinct Syntheses of Methopholine, (±)‐Homolaudanosine, and (±)‐Dysoxyline via Metal‐free One‐Pot Double Alkylation on 1‐Methyl‐3,4‐dihydroisoquinolines

Achary

Kim

Choi

et al. 2019

Bulletin Korean Chem Soc

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A mild one-pot and metal-free condition was discovered to implement two different alkyl groups chemoselectively on 1-methyl-3,4-dihydroisoquinoline (1-Me-DHIQ), one at the nitrogen another at the C1-methyl group. This chemistry is compatible with various DHIQs as well as alkyl halides. Application of this chemistry facilitated the concise syntheses of methopholine, (AE)-homolaudanosine, and (AE)-dysoxyline, requiring only two steps from 6,7-dimethoxy-1-Me-DHIQ.

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Design, synthesis, and biological evaluation of novel tetrahydroisoquinoline derivatives as potential antitumor candidate

Cited by 17 publications

References 25 publications

Technological Innovations in Disease Management: Text Mining US Patent Data From 1995 to 2017

Technological Innovations in Disease Management: Text Mining US Patent Data From 1995 to 2017

A Facile One‐Pot Synthesis of 1,2,3,4‐Tetrahydroisoquinoline‐1‐carbonitriles via the Electrogenerated Cyanide Anions from Acetonitrile

Succinct Syntheses of Methopholine, (±)‐Homolaudanosine, and (±)‐Dysoxyline via Metal‐free One‐Pot Double Alkylation on 1‐Methyl‐3,4‐dihydroisoquinolines

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