6,7-Dihydro[1,4]dioxino[2,3-f][1,3]benzothiazol-2-amine
[CAS# 313223-82-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: 6,7-Dihydro[1,4]dioxino[2,3-f][1,3]benzothiazol-2-amine
• Molecular Formula: C₉H₈N₂O₂S
• Molecular Weight: 208.24
• CAS Registry Number: 313223-82-4
• EC Number: 853-796-4
• SMILES: C1COC2=C(O1)C=C3C(=C2)SC(=N3)N

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

6,7-Dihydro[1,4]dioxin[2,3-f][1,3]benzothiazol-2-amine is a synthetic compound that has attracted much attention in the field of medicinal chemistry. The discovery of this molecule can be traced back to efforts aimed at developing novel therapeutic agents by exploiting the unique properties of heterocyclic compounds. Heterocycles, rings composed of at least one atom other than carbon, have been central to drug discovery due to their diverse biological activities. Among them, benzothiazoles stand out due to their established roles in a variety of pharmacological contexts, including anticancer, antimicrobial, and neuroprotective activities.

The synthesis of 6,7-dihydro[1,4]dioxin[2,3-f][1,3]benzothiazol-2-amine involves multiple steps, beginning with the formation of the benzothiazole core. This core was chosen for its biological relevance and potential to form stable and biologically active derivatives. The researchers then introduced the dioxin group, a chemical modification designed to enhance the stability and activity of the molecule. The introduction of this group was achieved via a cyclization reaction, a process that forms a ring structure by joining the two ends of the molecule. Following this, an amination process (adding an amine group (-NH2) to the structure) completes the synthesis to give 6,7-dihydro[1,4]dioxin[2,3-f][1,3]benzothiazol-2-amine.

The biological potential of this compound has been highlighted in various studies, with some of the most promising applications being in the field of cancer treatment. The molecule has shown the ability to target specific pathways involved in cancer cell proliferation and survival. One of its key mechanisms is the induction of apoptosis, a form of programmed cell death that is often defective in cancer cells, causing them to grow uncontrollably. By reactivating this pathway, 6,7-dihydro[1,4]dioxin[2,3-f][1,3]benzothiazol-2-amine has the potential to inhibit tumor growth and reduce the spread of cancer. What makes this compound particularly attractive is its selective toxicity, meaning it can target cancer cells while sparing normal healthy cells, thereby reducing the side effects that often accompany chemotherapy.

In addition to its anticancer activity, this compound has also been studied for its neuroprotective properties. In neurodegenerative diseases such as Alzheimer's and Parkinson's, certain cellular processes become dysregulated, leading to neuronal death. Research suggests that 6,7-dihydro[1,4]dioxin[2,3-f][1,3]benzothiazol-2-amine may interact with brain receptors and proteins involved in these processes, potentially offering a way to slow or halt the progression of these diseases. This dual activity in oncology and neurology makes the compound a particularly valuable target for drug development.

Another important area where this molecule shows promise is in the fight against microbial infections. The rise in antibiotic-resistant bacteria urgently requires new antimicrobial agents. Preliminary studies show that 6,7-dihydro[1,4]dioxin[2,3-f][1,3]benzothiazol-2-amine exhibits activity against a range of bacterial strains, including some that are resistant to current antibiotics. This activity, coupled with its relatively low toxicity to human cells, suggests that this compound could be developed into a new class of antibiotics that could help address one of the most pressing public health challenges of our time.

As research on 6,7-dihydro[1,4]dioxin[2,3-f][1,3]benzothiazol-2-amine continues, scientists are working to optimize its structure to improve its therapeutic potential. This involves modifying the molecule in various ways to enhance its activity, reduce any potential side effects, and improve its ability to be absorbed and utilized by the body. These efforts are part of a broader trend in medicinal chemistry, where the goal is not only to discover new drugs, but also to improve them to maximize benefit to patients.

In summary, 6,7-dihydro[1,4]dioxin[2,3-f][1,3]benzothiazol-2-amine represents a promising advance in the field of drug discovery. Its unique chemical structure and multifaceted biological activities make it a candidate for further study as a potential therapeutic agent in multiple areas of medicine. As research continues, it may one day contribute to the development of new treatments for cancer, neurodegenerative diseases, and antibiotic-resistant infections.