1469-28-9

Basic information

• Product Name: 8-Chlorodibenzo[b,f]thiepin-10(11H)-one
• Synonyms: 8-Chloro-10,11-dihydrodibenzo[b,f]thiepin-10-one;8-Chloro-10,11-dihydrodibenzo[b,f]thiepin-2-one
• CAS NO: 1469-28-9
• Molecular Formula: C₁₄H₉ClOS
• Molecular Weight: 260.73866
• Mol File: 1469-28-9.mol

Chemical Properties

• Melting Point: 125-126℃ (ethanol )
• Boiling Point: 425.8 °C at 760 mmHg
• Flash Point: 211.3 °C
• Appearance: /
• Density: 1.359 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 8-Chlorodibenzo[b,f]thiepin-10(11H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Chlorodibenzo[b,f]thiepin-10(11H)-one(1469-28-9)
• EPA Substance Registry System: 8-Chlorodibenzo[b,f]thiepin-10(11H)-one(1469-28-9)

Safety Data

• Hazardous Substances Data: 1469-28-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-Chlorodibenzo[b,f]thiepin-10(11H)-one is used as an intermediate in the synthesis of Zotepine-d6 for the development of atypical antipsychotic drugs. It is particularly important for the creation of Zotepine (Z700900), which is utilized in the treatment of acute and chronic schizophrenia, as well as acute bipolar mania. The compound acts as an antagonist at dopamine and serotonin receptors, with a high affinity for the D1 and D2 receptors, making it a valuable component in the development of effective psychiatric medications.

Upstream product

• 106-54-7 p-Chlorothiophenol 
• 18698-96-9 o-iodophenylacetic acid 
• 13459-62-6 2-[2-(4-chlorophenyl)sulfanylphenyl]acetic acid 

Downstream Products

• 58722-05-7 4-Chlordiphenylsulfoxid-2,2'-dicarboxylic acid 
• 13448-22-1 octoclothepin 
• 65999-60-2 2-chloro-10,11-dihydrodibenzothiepin-10,11-dione 

Relevant articles and documents

DIHYDROBENZO[B][1]BENZOTHIEPIN COMPOUNDS USEFUL IN THERAPY

The present invention relates to the use of a compound of formula (I), to decrease or inhibit, in vitro or ex vivo, the Patched receptor drug efflux activity, in particular the chemotherapeutic drug efflux activity and chemotherapy resistance. The present disclosure further relates to uses of such compounds, in particular to prepare a pharmaceutical composition to allow or improve the efficiency of a therapy of cancer in a subject in need thereof. The compound of the invention can indeed be advantageously used, in combination with at least one chemotherapeutic drug, for treating cancer, for preventing cancer metastasis and/or for preventing cancer recurrence in a subject.

Overcoming chloroquine resistance in malaria: Design, synthesis and structure-activity relationships of novel chemoreversal agents

Malaria remains a significant infectious disease with even artemisinin-based therapies now facing resistance in the field. Development of new therapies is urgently needed, either by finding new compounds with unique modes of action, or by reversing resistance towards known drugs with 'chemosensitizers' or 'chemoreversal' agents (CRA). Concerning the latter, we have focused on the resistance mechanisms developed against chloroquine (CQ). We have synthesized a series of compounds related to previously identified CRAs, and found promising novel compounds. These compounds show encouraging results in a coumarin labeled chloroquine uptake assay, exhibiting a dose response in resensitising parasites to the antimalarial effects of chloroquine. Selected compounds show consistent potency across a panel of chloroquine and artemisinin sensitive and resistant parasites, and a wide therapeutic window. This data supports further study of CRAs in the treatment of malaria and, ultimately, their use in chloroquine-based combination therapies.

Exploring the neuroleptic substituent in octoclothepin: Potential ligands for positron emission tomography with subnanomolar affinity for α1-adrenoceptors

A series of 1-(10,11-dihydrodibenzo[b,f]thiepin-10-yl)-4-methylpiperazine analogues substituted in the 8-position of the 10,11-dihydrodibenzo[b,f]thiepine scaffold with aryl, heteroaryl, amine, and amide substituents are described. The compounds were designed using the previously reported Liljefors- B?ges? pharmacophore model for dopamine D2 and α1-adrenoceptor antagonists, with the aim of obtaining selective α1-adrenoceptor antagonists suitable for development as radioligands for imaging of central α1-adrenoceptors by positron emission tomography. Sixteen aryl and heteroaryl substituted octoclothepin analogues were prepared by a convergent synthesis via coupling of 1-methyl-4-(8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10, 11-dihydrodibenzo[b,f]thiepin-10-yl)piperazine with aryl and heteroaryl halides under palladium catalysis. The most selective compound obtained, (S)-N-((11-(4-methylpiperazin-1-yl)-10,11-dihydrodibenzo[b,f]thiepin-2-yl) methyl)isobutyramide (S)-35, showed a similar subnanomolar affinity compared to α1a, α1b, and α1d- adrenoceptors and a selectivity ratio of 20, 440, and 20 with respect to D 2, 5-HT2C, and H1 receptors, respectively.