111423-07-5

Upstream product

• 85716-87-6 ethyl 2-isothiocyanato-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 106-47-8 4-chloro-aniline 
• 108-94-1 cyclohexanone 
• 105-56-6 ethyl 2-cyanoacetate 
• 4506-71-2 ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 2131-55-7 4-Chlorophenyl isothiocyanate 

Downstream Products

• 111423-08-6 3-(4-chloro-phenyl)-2-mercapto-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 934246-66-9 3-(4-chlorophenyl)-2-hydrazino-5,6,7,8-tetrahydrobenzo(b)thiophene[2,3-d]pyrimidine-4(3H)-one 
• 144846-33-3 2-[3-(4-Chloro-phenyl)-4-phenyl-3H-thiazol-(2Z)-ylideneamino]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 111423-08-6 3-(4-chlorophenyl)-2-thioxo-2,3,5,6,7,8-hexahydro-1H-benzo[4,5]thieno[2,3-d]-pyrimidin-4-one 
• 144846-34-4 2-[3-(4-Chloro-phenyl)-4-(4-nitro-phenyl)-3H-thiazol-(2Z)-ylideneamino]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 168280-55-5 3-amino-2-(4-chlorophenyl)amino-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 

Relevant academic research and scientific papers

Design, Synthesis, and Structure-Activity Relationship of N-Aryl- N′-(thiophen-2-yl)thiourea Derivatives as Novel and Specific Human TLR1/2 Agonists for Potential Cancer Immunotherapy

The previous virtual screening of ten million compounds yielded two novel nonlipopeptide-like chemotypes as TLR2 agonists. Herein, we present the chemical optimization of our initial hit, 1-phenyl-3-(thiophen-2-yl)urea, which resulted in the identification of SMU-C80 (EC50 = 31.02 ± 1.01 nM) as a TLR2-specific agonist with a 370-fold improvement in bioactivity. Mechanistic studies revealed that SMU-C80, through TLR1/2, recruits the adaptor protein MyD88 and triggers the NF-κB pathway to release cytokines such as TNF-α and IL-1β from human, but not murine, cells. To the best of our knowledge, it is the first species-specific TLR1/2 agonist reported until now. Moreover, SMU-C80 increased the percentage of T, B, and NK cells ex vivo and activated the immune cells, which suppressed cancer cell growth in vitro. In summary, we obtained a highly efficient and specific human TLR1/2 agonist that acts through the MyD88 and NF-κB pathway, facilitating cytokine release and the simultaneous activation of immune cells that in turn affects the apoptosis of cancer cells.

Novel thienopyrimidine-aminothiazole hybrids: Design, synthesis, antimicrobial screening, anticancer activity, effects on cell cycle profile, caspase-3 mediated apoptosis and VEGFR-2 inhibition

A series of novel hybrid compounds of hexahydrobenzo[4,5]thieno[2,3-d]pyrimidine with aminothiazole scaffolds were synthesized. The synthesized compounds were evaluated for their cytotoxic activity against the NCI-60 human tumor cell line panel. Compounds 7c, 7d and 7e exhibited significant antiproliferative activities at 10?5 M dose. Compound 7c exhibited excellent cytotoxic activity against CNS cancer cell lines including SNB-75 and SF-295 as well as renal cancer cell line CAKI-1 when compared with sorafenib as standard anticancer drug. In addition, compound 7d showed almost comparable anticancer activity to sorafenib against SNB-75 cell line and displayed moderate activity against SF-295 and CAKI-1 cell lines in comparison to sorafenib. Compound 7c inhibited the vascular endothelial growth factor receptor 2 (VEGFR-2) with IC50 of 62.48 ± 3.7 nM and decreased both total VEGFR-2 and phosphorylated VEGFR-2 in treated SNB-75 cells suggesting its ability to down regulate cell proliferation, growth, and survival. The flow cytometric analysis showed that 7c displayed its cytotoxic activity through the reduction of the cellular proliferation and induction of cell cycle arrest at the G2/M phase. Compound 7c clearly boosted the level of the apoptotic caspase-3. All the synthesized compounds were also screened for their antibacterial and antifungal activity against four pathogenic strains of both Gram-positive and Gram-negative as well as Candida albicans. Only compound 7d exhibited antifungal activity against Candida albicans compared to nystatin as the standard antifungal compound.

Synthesis, characterization and biological studies of some novel thieno[2,3-d]pyrimidines

Several 2-unsubstituted thieno[2,3-d]pyrimidines have been prepared from 2-aminothiophene-3-carboxylic acid esters and their carbonitrile analogs. Some triazolothienopyrimidine and 2-thioxothienopyrimidine representatives have also been synthesized using

Facile synthesis of 2-alkylthio-5,6,7,8-tetrahydrobenzothieno[2,3-d]- Pyrimidin-4(3H)-ones

Isothiocyanate 2, obtained from aza-Wittig reaction of iminophosphorane 1 with CS2, reacted with amine to give 2-thioxo-2,3,5,6,7,8- hexahydrobenzothieno[2,3-d]pyrimidin-4(1H)-ones 4 in the presence of sodium ethoxide. S-Alkylation of 4 produced 2-alkylth

Structure-activity relationship analysis of a novel necroptosis inhibitor, Necrostatin-5

Necrostatin-5 (Nec-5) is a novel potent small-molecule inhibitor of necroptosis structurally distinct from previously described Necrostatin-1 (Nec-1), and therefore, represents a new direction for the inhibition of this cellular caspase-independent necrot

Synthesis of some thienopyrimidine derivatives

Thioxothienopyrimidinones, alkylthio- and arylalkylthiothienopyrimidinones, thienopyrimidinones, thienopyrimidines a thienopyrimidinedione and a thienotriazolopyrimidinone were prepared from 2-amino-3-carboethoxy-4,5- disubstituted thiophenes and 2-amino-

Synthesis and antimicrobial activity of some thiazolinyl tetrahydrobenzo[b]thiophenes and thiazolinyl tetrahydrobenzothieno[2,3-d]pyrimidin-4-ones

Two series of novel 3-carbethoxy-2-(3',4'-disubstituted-2',3'-dihydrothiazol-2'-ylidenamin o)-4,5,6,7-tetrahydrobenzo[b]thiophenes (3a-o) and 2-methyl-3-(3',4'-disubstituted-2',3'-dihydrothiazol-2'-ylidenamino-5, 6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidi

METHYL N-ARYLDITHIOCARBAMATES: USEFUL REAGENTS FOR THE ANNELATION OF PYRIMIDINES AND 1,3-OXAZINES TO FIVE-MEMBERED HETEROCYCLIC RINGS

The reaction of methyl N-aryldithiocarbamates with ?-excessive heteroaromatic o-amino acid derivatives leads to the annelation of 4-oxo-2-thioxopyrimidines, 2,4-dioxopyrimidines or 2-arylamino-1,3-oxazines, depending on the reaction conditions.