Design, synthesis, and biological evaluation of novel sulfamoylbenzamide derivatives as HBV capsid assembly modulators

Wang, Shuo; Ren, Yujie; Li, Qilan; Wang, Ya; Jiang, Xiangyi; Xu, Shujing; Zhang, Xujie; Zhao, Shujie; Bradley, Daniel P.; Woodson, Molly; Zhao, Fabao; Wu, Shuo; Li, Yuhuan; Tian, Ye; Liu, Xinyong; Tavis, John E.; Zhan, Peng

doi:10.1016/j.bioorg.2022.106192

Cited by 3 publications

(4 citation statements)

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“…These findings provide a promising starting point for future studies to promote the development of safer and more potent CAMs for treating HBV infection [106]. In 2022, Wang et al from Shandong University in China reported the modification of NVR-3778 compounds [107]. The solvent-exposed region of these derivatives was modified to include phenylboronic acid (38) or phenylboronate ester groups as mentioned in Figure 9.…”

Section: Sulfamoyl Benzocarboxamides As Camsmentioning

confidence: 97%

“…Since 2014, dynamic research on SBAs has yielded invaluable insights into the SARs of diverse components linked to sulfonamide side chains and changes in core substituents [94][95][96][97][98][99][100][101][102][103][104][105][106][107][108]. In 2014, Janssen researched sulfamoyl aryl carboxamides, focusing on the aniline portions of amides and the amine components of sulfonamides.…”

Section: Sulfamoyl Benzocarboxamides As Camsmentioning

confidence: 99%

“…In 2022, Wang et al from Shandong University in China reported the modification of NVR-3778 compounds [107]. The solvent-exposed region of these derivatives was modified to include phenylboronic acid (38) or phenylboronate ester groups as mentioned in Figure 9.…”

Section: Sulfamoyl Benzocarboxamides As Camsmentioning

confidence: 99%

“…However, the clearance rate of the orally administered drug was significantly higher than that of the intravenously administered drug. As a result, bioavailability was only 2.85% [107]. Further efforts by the same laboratory to make NVR 3-778 more soluble in water led Xiangkai et al to synthesize many unique prodrugs of phosphate (40) and carboxylic acid (41).…”

Section: Sulfamoyl Benzocarboxamides As Camsmentioning

confidence: 99%

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Recent Advances in the Development of Sulfamoyl-Based Hepatitis B Virus Nucleocapsid Assembly Modulators

Nayak,

Gowda,

Abbas

et al. 2023

Viruses

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Hepatitis B virus (HBV) is the primary contributor to severe liver ailments, encompassing conditions such as cirrhosis and hepatocellular carcinoma. Globally, 257 million people are affected by HBV annually and 887,000 deaths are attributed to it, representing a substantial health burden. Regrettably, none of the existing therapies for chronic hepatitis B (CHB) have achieved satisfactory clinical cure rates. This issue stems from the existence of covalently closed circular DNA (cccDNA), which is difficult to eliminate from the nucleus of infected hepatocytes. HBV genetic material is composed of partially double-stranded DNA that forms complexes with viral polymerase inside an icosahedral capsid composed of a dimeric core protein. The HBV core protein, consisting of 183 to 185 amino acids, plays integral roles in multiple essential functions within the HBV replication process. In this review, we describe the effects of sulfamoyl-based carboxamide capsid assembly modulators (CAMs) on capsid assembly, which can suppress HBV replication and disrupt the production of new cccDNA. We present research on classical, first-generation sulfamoyl benzocarboxamide CAMs, elucidating their structural composition and antiviral efficacy. Additionally, we explore newly identified sulfamoyl-based CAMs, including sulfamoyl bicyclic carboxamides, sulfamoyl aromatic heterocyclic carboxamides, sulfamoyl aliphatic heterocyclic carboxamides, cyclic sulfonamides, and non-carboxamide sulfomoyl-based CAMs. We believe that certain molecules derived from sulfamoyl groups have the potential to be developed into essential components of a well-suited combination therapy, ultimately yielding superior clinical efficacy outcomes in the future.

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Section: Sulfamoyl Benzocarboxamides As Camsmentioning

confidence: 97%