Production Method 1

53827-52-4

864169-35-7

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ,  Phosphorus pentachloride ;  3 h, heated
1.2 Reagents: Water ;  cooled

Reference

Synthesis, anti-inflammatory and antinociceptive activity of some novel benzothiazole derivatives

Abbas, Eman M. H.; et al, Research on Chemical Intermediates, 2015, 41(4), 2537-2555

Production Method 2

6294-52-6

864169-35-7

Reaction Conditions

1.1 Reagents: tert-Butyl nitrite ,  Cupric chloride Solvents: Acetonitrile ;  0 °C; 1 h, rt; 1 h, 65 °C

Reference

Synthesis of APTRA derivatives as building blocks for low-affinity fluorescent Ca2+ indicators

Metten, Bert; et al, Synthesis, 2005, (11), 1838-1844

Production Method 3

6294-52-6

864169-35-7

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Phosphoric acid Solvents: Water ;  2 h, -10 - 0 °C
1.2 Reagents: Sodium chloride ,  Copper sulfate Solvents: Water ;  2 h, -5 °C

Reference

The first potent inhibitors for human glutaminyl cyclase: synthesis and structure-activity relationship

Buchholz, Mirko; et al, Journal of Medicinal Chemistry, 2006, 49(2), 664-677

Production Method 4

6315-89-5

333-20-0

864169-35-7

Reaction Conditions

1.1 Reagents: Bromine Solvents: Acetic acid ,  Water ;  10 h, 35 °C
1.2 Reagents: Ammonium hydroxide Solvents: Water ;  neutralized, rt
2.1 Reagents: Sodium nitrite ,  Phosphoric acid Solvents: Water ;  2 h, -10 - 0 °C
2.2 Reagents: Sodium chloride ,  Copper sulfate Solvents: Water ;  2 h, -5 °C

Reference

The first potent inhibitors for human glutaminyl cyclase: synthesis and structure-activity relationship

Buchholz, Mirko; et al, Journal of Medicinal Chemistry, 2006, 49(2), 664-677

Production Method 5

6315-89-5

505-14-6

864169-35-7

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Methanol ;  30 min, rt
2.1 Reagents: tert-Butyl nitrite ,  Cupric chloride Solvents: Acetonitrile ;  0 °C; 1 h, rt; 1 h, 65 °C

Reference

Synthesis of APTRA derivatives as building blocks for low-affinity fluorescent Ca2+ indicators

Metten, Bert; et al, Synthesis, 2005, (11), 1838-1844

2-chloro-5,6-dimethoxy-1,3-benzothiazole Raw materials

• 4-Aminoveratrol
• Potassium thiocyanate
• azanylidyne-cyanodisulfanyl-methane
• 5,6-dimethoxy-1,3-benzothiazol-2-amine
•  

2-chloro-5,6-dimethoxy-1,3-benzothiazole Preparation Products

• 2-chloro-5,6-dimethoxy-1,3-benzothiazole (864169-35-7)

• 1. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203
• 2. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
• 3. Dissolution of cork biopolymers in biocompatible ionic liquids
  Helga Garcia,Rui Ferreira,Marija Petkovic,Jamie L. Ferguson,Maria C. Leit?o,H. Q. Nimal Gunaratne,Luís Paulo N. Rebelo Green Chem., 2010,12, 367-369
• 4. Enantiocontrolled construction of sistodiolynne, an unusual polyketide from the wood-decay fungus Sistrema raduloides
  Chem. Commun., 1997, 767-768
• 5. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzothiazoles Benzothiazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzothiazoles

Recent Advances in the Study of 2-Chloro-5,6-dimethoxy-1,3-benzothiazole (CAS: 864169-35-7) in Chemical Biology and Pharmaceutical Research

The compound 2-chloro-5,6-dimethoxy-1,3-benzothiazole (CAS: 864169-35-7) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This heterocyclic compound, characterized by a benzothiazole core with chloro and dimethoxy substituents, has been the subject of several studies exploring its biological activity, synthetic utility, and mechanism of action. The following research brief consolidates the latest findings related to this compound, providing insights into its current and future applications.

Recent studies have highlighted the role of 2-chloro-5,6-dimethoxy-1,3-benzothiazole as a versatile intermediate in the synthesis of bioactive molecules. Its electron-rich aromatic system and reactive chloro substituent make it an attractive building block for the development of novel pharmaceuticals. For instance, researchers have utilized this compound in the synthesis of kinase inhibitors, where its structural motif contributes to binding affinity and selectivity. Additionally, its potential as a scaffold for antimicrobial and anti-inflammatory agents has been explored, with promising results in preliminary in vitro assays.

One of the most notable advancements involves the investigation of 2-chloro-5,6-dimethoxy-1,3-benzothiazole in neurodegenerative disease research. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibit inhibitory activity against key enzymes implicated in Alzheimer's disease, such as acetylcholinesterase and beta-secretase. The study employed molecular docking and kinetic assays to elucidate the binding interactions, revealing that the chloro and dimethoxy groups play a critical role in enzyme inhibition. These findings suggest a potential pathway for developing new therapeutic agents targeting neurodegenerative disorders.

Another area of interest is the compound's application in cancer research. Recent preclinical studies have shown that 2-chloro-5,6-dimethoxy-1,3-benzothiazole derivatives can modulate signaling pathways involved in cell proliferation and apoptosis. For example, a 2022 study in Bioorganic & Medicinal Chemistry Letters reported that certain analogs of this compound exhibited potent activity against breast cancer cell lines, with IC50 values in the low micromolar range. Mechanistic studies indicated that these compounds induce cell cycle arrest and activate apoptotic pathways, highlighting their potential as anticancer agents.

In addition to its therapeutic potential, 2-chloro-5,6-dimethoxy-1,3-benzothiazole has also been investigated for its utility in chemical biology tools. Researchers have leveraged its fluorescent properties to develop probes for studying protein-ligand interactions and cellular processes. A 2023 study in ACS Chemical Biology described the synthesis of a fluorescent derivative of this compound, which was used to visualize the localization of specific proteins in live cells. This application underscores the compound's versatility beyond traditional drug discovery.

Despite these promising developments, challenges remain in the optimization and clinical translation of 2-chloro-5,6-dimethoxy-1,3-benzothiazole-based compounds. Issues such as bioavailability, metabolic stability, and off-target effects need to be addressed through further structure-activity relationship (SAR) studies and medicinal chemistry optimization. Future research directions may include the development of prodrug strategies, formulation improvements, and combination therapies to enhance efficacy and reduce toxicity.

In conclusion, 2-chloro-5,6-dimethoxy-1,3-benzothiazole (CAS: 864169-35-7) represents a valuable scaffold in chemical biology and pharmaceutical research, with demonstrated applications in neurodegenerative disease, cancer, and chemical probe development. Continued exploration of its derivatives and mechanisms of action is expected to yield new therapeutic candidates and tools for biomedical research. The compound's multifaceted potential positions it as a key player in the advancement of precision medicine and targeted therapies.

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