67171-55-5

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 2-AMINO-4-PHENYLTHIOPHENE-3-CARBOXYLATE is used as a reactant for the synthesis of thienopyrimidine-based FLT3 inhibitors. FLT3 inhibitors are a class of drugs that target the FMS-like tyrosine kinase 3 (FLT3) receptor, which is often mutated in acute myeloid leukemia (AML) and other hematologic malignancies. METHYL 2-AMINO-4-PHENYLTHIOPHENE-3-CARBOXYLATE plays a crucial role in the development of these targeted therapies, offering a potential treatment option for patients with FLT3-mutated cancers.

Upstream product

• 98-86-2 acetophenone 
• 14505-27-2 Methyl-α-cyano-β-methyl-β-phenylacrylat 
• 105-34-0 methyl 2-cyanoacetate 

Downstream Products

• 126080-29-3 methyl 2-methoxycarbonylamino-4-phenylthiophene-3-carboxylate 
• 126080-05-5 6-Phenyl-2,3-dihydro-oxazolo[3,2-a]thieno[2,3-d]pyrimidin-5-one 
• 126080-28-2 methyl 2-(2-oxo-1-imidazolidinyl)-4-phenylthiophene-3-carboxylate 
• 935760-34-2 ethyl 4-oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate 
• 935759-47-0 4-oxo-5-phenyl-N-{3-[2-(1H-1,2,4-triazol-3-yloxy)ethoxy]-benzyl}-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide 
• 1622230-19-6 C₁₈H₁₃N₃OS 
• 1622230-18-5 C₂₀H₁₇N₃OS 
• 1622230-17-4 C₁₉H₁₄N₂O₂S 
• 1622230-24-3 C₁₈H₁₅N₅S 
• 1622230-23-2 C₂₀H₁₉N₅S 
• 1622230-22-1 C₁₉H₁₆N₄OS 

Relevant academic research and scientific papers

Synthesis of novel 2-(1-adamantanylcarboxamido)thiophene derivatives. Selective cannabinoid type 2 (CB2) receptor agonists as potential agents for the treatment of skin inflammatory disease

A set of CB2R ligands, based on the thiophene scaffold, was synthesized and evaluated in in vitro assays. Compounds 8c-i, k, l, bearing the 3-carboxylate and 2-(adamantan-1-yl)carboxamido groups together with apolar alkyl/aryl substituents at 5-position or at 4- and 5-positions of the thiophene ring possess high CB2R affinity at low nanomolar concentration, good receptor selectivity, and agonistic functional activity. The full agonist 8g, showing the best balance between receptor affinity and selectivity, was tested in vitro in an experimental model of allergic contact dermatitis and proved to be able to block the release of MCP-2 in HaCaT cells at 10 μM concentration.

Design, Synthesis, and SAR Studies of Heteroarylpyrimidines and Heteroaryltriazines as CB2R Ligands

Herein we describe the design and synthesis of a new series of heteroarylpyrimidine/heteroaryltriazine derivatives on the basis of quinazoline-2,4(1H,3H)-diones as CB2R-selective ligands using a bioisosterism strategy. An acetamide group was explored to displace the enamine linker of the lead compound for the purpose of stereoisomerism elimination and hydrophilicity increase. As a result, some of the synthesized compounds showed high bioactivity and selectivity for CB2R in calcium mobilization assays, and four displayed CB2R agonist activity, with EC50 values below 30 nm. The compound exhibiting the highest agonist activity toward CB2R (EC50=7.53±3.15 nm) had a selectivity over CB1R of more than 1328-fold. Moreover, structure–activity relationship (SAR) studies indicated that the substituents on the nucleus play key roles in the functionality of a ligand, with one such example demonstrating CB2R antagonist activity. Additionally, molecular docking simulations were conducted with the aim of better understanding of these new derivatives in relation to the structural requirements for agonists/antagonists binding to CB2R.

Heteroarylpyrimindinedione derivative and use thereof

The invention provides a heteroarylpyrimindinedione derivative and use thereof. The heteroarylpyrimindinedione derivative comprises a compound with a structure shown as general formula I, and a pharmaceutically acceptable salt or hydrate thereof. The derivative is obtained by chemical synthesis, and pharmacological experiments prove that the active ligand with cannabinoid type II receptor CB2 can be used for preparation of drugs for prevention and mitigation of CB2 receptor-mediated diseases, and the drug is cannabinoid CB2 receptor agonist's agonist, partial agonist, inverse agonist or antagonist. And the general structural formula I is shown as the specification.

Discovery of thienopyrimidine-based FLT3 inhibitors from the structural modification of known IKKβ inhibitors

Inactivation of the NF-κB signaling pathway by inhibition of IKKβ is a well-known approach to treat inflammatory diseases such as rheumatoid arthritis and cancer. Thienopyrimidine-based analogues were designed through modification of the known IKKβ inhibitor, SPC-839, and then biologically evaluated. The resulting analogues had good inhibitory activity against both nitric oxide and TNF-α, which are well-known inflammatory responses generated by activated NF-κB. However, no inhibitory activity against IKKβ was observed with these compounds. The thienopyrimidine-based analogues were subsequently screened for a target kinase, and FLT3, which is a potential target for acute myeloid leukemia (AML), was identified. Thienopyrimidine-based FLT3 inhibitors showed good inhibition profiles against FLT3 under 1 μM. Overall, these compounds represent a promising family of inhibitors for future development of a treatment for AML.

Synthesis and biological evaluation of novel thieno[2,3-d[pyrimidine-based FLT3 inhibitors as anti-leukemic agents

The most common mutations in acute myeloid leukemia (AML) are those that cause the activation of FMS-like tyrosine kinase 3 (FLT3). Therefore, FLT3 is regarded as a potential target for the treatment of AML. A novel series of thieno[2,3-d]pyrimidine-based analogs was designed and synthesized as FLT3 inhibitors. All synthesized compounds were assayed for the tyrosine kinase activity of FLT3 and growth inhibitory activity in four human leukemia cell lines (THP1, MV4-11, K562, and HL-60). Among these compounds, compound 17a, which possesses relatively short and simple substituents at the C6 position of thieno[2,3-d]pyrimidine, emerged as the most promising anti-leukemic agent. Compound 17a exhibited potent inhibition of FLT3-positive leukemic cell growth and of the FLT3 D835Y kinase; such inhibition is required for the successful treatment of AML. The data supports the further investigation of this class of compounds as potential anti-leukemic agents.

Synthesis and biological evaluation of novel thieno[2,3-d]pyrimidine-based FLT3 inhibitors as anti-leukemic agents

The most common mutations in acute myeloid leukemia (AML) are those that cause the activation of FMS-like tyrosine kinase 3 (FLT3). Therefore, FLT3 is regarded as a potential target for the treatment of AML. A novel series of thieno[2,3-d]pyrimidine-based analogs was designed and synthesized as FLT3 inhibitors. All synthesized compounds were assayed for the tyrosine kinase activity of FLT3 and growth inhibitory activity in four human leukemia cell lines (THP1, MV4-11, K562, and HL-60). Among these compounds, compound 17a, which possesses relatively short and simple substituents at the C6 position of thieno[2,3-d]pyrimidine, emerged as the most promising anti-leukemic agent. Compound 17a exhibited potent inhibition of FLT3-positive leukemic cell growth and of the FLT3 D835Y kinase; such inhibition is required for the successful treatment of AML. The data supports the further investigation of this class of compounds as potential anti-leukemic agents.

Synthesis of some novel methyl- and ethyl-2-aminothiophene-3-carboxylate and related Schiff-bases

Methyl- and ethyl-2-amino thiophene-3-carboxylate derivatives 1(a-h) were synthesized by a simple one-pot condensation reaction of the ketone, elemental sulphur and methyl- or ethylcyanoacetate in the presence of morpholine as a catalyst. Further reaction of these compounds with salicylaldehyde gave related Schiff-bases, 2(a-e). Yields of products following recrystallization from ethanol were in the range of 70-85 %. 1H NMR and IR spectra and elemental analysis data were used to identification of these compounds.

NOVEL THIENOPYRIMIDINE DERIVATIVES OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention relates to a novel thienopyrimidine derivative having an excellent anti? inflammatory and anti-cancer activity, or a pharmaceutically acceptable salt thereof, a process for the preparation thereof and a pharmaceutical composition comprising the same. The compound according to the present invention strongly inhibits IKB kinase-β (IKK-β) involved in the activation of a transcriptional factor, NF-κB, which is associated with inducing various immune and inflammatory diseases, whereby a composition comprising the compound is a useful therapeutic agent against inflammatory diseases, in particular, arthritis and cancer.