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Cas Database

4815-36-5

4815-36-5

Identification

  • Product Name:3-Thiophenecarboxylicacid, 2-amino-4-phenyl-, ethyl ester

  • CAS Number: 4815-36-5

  • EINECS:

  • Molecular Weight:247.318

  • Molecular Formula: C13H13NO2S

  • HS Code:29349990

  • Mol File:4815-36-5.mol

Synonyms:2-Amino-3-(ethoxycarbonyl)-4-phenylthiophene;2-Amino-3-carboethoxy-4-phenylthiophene;Ethyl 2-amino-4-phenyl-3-thiophenecarboxylate;NSC 149683;NSC 171773;

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Safety information and MSDS

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

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  • Manufacture/Brand:Usbiological
  • Product Description:Ethyl 2-Amino-4-phenylthiophene-3-carboxylate
  • Packaging:100mg
  • Price:$ 305
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  • Manufacture/Brand:TRC
  • Product Description:Ethyl 2-amino-4-phenylthiophene-3-carboxylate
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Ethyl 2-amino-4-phenylthiophene-3-carboxylate 97%
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-Amino-4-phenyl-3-thiophenecarboxylic acidethyl ester 95+%
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-Amino-4-phenyl-3-thiophenecarboxylic acidethyl ester 95+%
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-Amino-4-phenyl-3-thiophenecarboxylic acidethyl ester 95+%
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  • Manufacture/Brand:Crysdot
  • Product Description:Ethyl 2-amino-4-phenylthiophene-3-carboxylate 96%
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  • Manufacture/Brand:Chemenu
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  • Manufacture/Brand:ChemBridge Corporation
  • Product Description:Ethyl 2-amino-4-phenylthiophene-3-carboxylate 95%
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  • Manufacture/Brand:Cayman Chemical
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Relevant articles and documentsAll total 42 Articles be found

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

Chen, Zhipeng,Zhang, Lina,Yang, Junjie,Zheng, Lu,Hu, Fanjie,Duan, Siqin,Nandakumar, Kutty Selva,Liu, Shuwen,Yin, Hang,Cheng, Kui

supporting information, p. 7371 - 7389 (2021/06/28)

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.

ECTONUCLEOTIDE PYROPHOSPHATASE/PHOSPHODIESTERASE 1 (ENPP1) MODULATORS AND USES THEREOF

-

Paragraph 00220; 00231; 00300, (2021/07/02)

Provided herein are small molecule modulators of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

Design, molecular docking and biological evaluation of fused thienopyrimidines and quinazoline

Kaliraj,Jeyalakshmi,Kathiravan,Madhavan,Devi, Arikketh

, p. 537 - 544 (2021/02/27)

The anticancer activity of the condensed pyrimidine and quinazoline moieties are pronounced with a different pathway. Thienopyrimidine is considered as ring equivalent bioisosteres of quinazolines and present in other heterocyclic compounds including thienopyrimidine. The present investigation focused on the synthesis of thienopyrimidine and quinazoline derivatives for their anticancer activity against the human oral squamous carcinoma-3 (HSC-3) cell line. The synthesized compound confirmed for their structural characteristics from spectral analysis and tested for anti-proliferative activity from MTT assay. The electron-withdrawing group in 4-chloro thienopyrimidines and amino ester derivate/facilitate the inhibition of cancer cells. Further probing by docking studies revealed that the compounds exhibit possible interactions with VEGF, FGFR and c-Met proteins, which are known to have a role in the pathogenesis of oral squamous cell carcinoma. Among the derivatives a moderate activity demonstrated by substituted 4-chloro-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]-pyrimidine (4a) and ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (1a) derivatives. Lack of chirality and the presence of bulky substituents in few of the compounds were found to be the cause for lower potency.

BENZOTHIADIAZINE DERIVATIVES AND COMPOSITIONS COMPRISING THE SAME FOR TREATING DISORDERS MEDIATED BY ADENOSINE

-

Page/Page column 30-31; 33, (2020/07/15)

Disclosed herein are novel inhibitors of CD73. More specifically, the novel CD73 inhibitors are derived from benzothiadiazine. Further, the present disclosure is related to the use of said benzothiadiazine derivatives in the treatment of diseases and/or d

Subtle modifications to a thieno[2,3-d]pyrimidine scaffold yield negative allosteric modulators and agonists of the dopamine D2 receptor

Fyfe, Tim J.,Kellam, Barrie,Mistry, Shailesh N.,Scammells, Peter J.,Lane, J. Robert,Capuano, Ben

, p. 474 - 490 (2019/03/07)

We recently described a structurally novel series of negative allosteric modulators (NAMs) of the dopamine D2 receptor (D2R) based on thieno[2,3-d]pyrimidine 1, showing it can be structurally simplified to reveal low molecular weight, fragment-like NAMs that retain robust negative cooperativity, such as 3. Herein, we report the synthesis and functional profiling of analogues of 3, placing specific emphasis on examining secondary and tertiary amino substituents at the 4-position, combined with a range of substituents at the 5/6-positions (e.g. aromatic/aliphatic carbocycles). We identify analogues with diverse pharmacology at the D2R including NAMs with sub-μM affinity (9h) and, surprisingly, low efficacy partial agonists (9d and 9i).

Process route upstream and downstream products

Process route

acetophenone
98-86-2

acetophenone

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate
4815-36-5

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate

Conditions
Conditions Yield
acetophenone; ethyl 2-cyanoacetate; With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.5h;
With pyridine; In dichloromethane; at 0 - 20 ℃;
With sulfur; diethylamine; In tetrahydrofuran; at 20 ℃; for 2h;
97%
With sulfur; In ethanol; at 78 ℃; for 0.916667h;
92%
With caesium carbonate; sulfur; In ethanol; for 2.5h; Reflux;
90%
acetophenone; ethyl 2-cyanoacetate; With morpholine; acetic acid; In toluene; at 125 ℃; for 24h; Dean-Stark;
With sulfur; diethylamine; In ethanol; at 50 ℃; for 3h;
86%
With morpholine; sulfur; In methanol; at 35 - 40 ℃; for 3.5h;
70%
With morpholine; sulfur; acetic acid; In ethanol; at 55 ℃;
68%
With morpholine; sulfur; In ethanol; at 90 ℃;
68%
With sulfur; In ethanol; Reflux;
68%
With morpholine; sulfur; In ethanol; at 60 ℃; for 12h; Inert atmosphere;
64%
With sulfur; potassium fluoride on basic alumina; In ethanol; at 100 ℃; for 0.125h; under 12928.7 Torr; microwave irradiation;
61%
With morpholine; sulfur; In ethanol; at 120 ℃; for 0.333333h; Microwave irradiation;
60%
With morpholine; sulfur; at 20 ℃; for 18h;
49%
With sulfur; In ethanol; for 4h; Reflux;
43%
With morpholine; aluminum oxide; sulfur; for 0.25h; Microwave irradiation;
27%
With sulfur; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 120 ℃; for 0.333333h; microwave irradiation;
With morpholine; sulfur; In ethanol; at 60 ℃;
With 4-methyl-morpholine; aluminum oxide; ammonium acetate; sulfur; for 0.166667h; Microwave irradiation; Neat (no solvent);
With sulfur; triethylamine; In diethyl ether; at 20 ℃; for 12h;
With morpholine; aluminum oxide; sulfur; for 0.25h; Microwave irradiation;
acetophenone; ethyl 2-cyanoacetate; With morpholine; acetic acid; In ethanol; at 55 ℃;
With sulfur; In ethanol; at 55 ℃;
With morpholine; sulfur; In ethanol; Reflux;
With sulfur; diethylamine; In ethanol; at 20 ℃; for 26h;
With morpholine; aluminum oxide; sulfur; at 120 ℃; for 0.25h; Microwave irradiation;
With sulfur; diethylamine; In methanol; at 100 ℃; Microwave irradiation;
acetophenone; ethyl 2-cyanoacetate; With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.5h;
With pyridine; In dichloromethane; at 20 ℃;
With sulfur; diethylamine; In tetrahydrofuran; at 20 ℃; for 2h;
With morpholine; sulfur; In ethanol; at 60 ℃;
With morpholine; sulfur; In ethanol; Reflux;
acetophenone; ethyl 2-cyanoacetate; With diethylamine; In ethanol; at 20 ℃;
With sulfur; In ethanol; at 20 ℃;
With morpholine; sulfur; In ethanol; at 20 ℃;
ethyl 2-cyano-3-phenylbut-2-enoate
14533-92-7,17277-47-3,18300-89-5

ethyl 2-cyano-3-phenylbut-2-enoate

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate
4815-36-5

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate

Conditions
Conditions Yield
With sulfur; diethylamine; In ethanol; for 1.5h;
76%
With sulfur; triethylamine;
65%
With morpholine; sulfur; In ethanol; for 14h; Heating / reflux;
50%
With sulfur; diethylamine; In ethanol; at 20 - 62 ℃; for 1.5h;
With sulfur; diethylamine; In ethanol; at 20 - 62 ℃; for 1.33333h;
With sulfur; diethylamine; In ethanol; at 50 ℃; for 18h;
With sulfur; triethylamine; In ethanol; at 50 ℃; for 2h;
(Z)-2-cyano-3-phenylbut-2-enoic acid ethyl ester
17277-47-3

(Z)-2-cyano-3-phenylbut-2-enoic acid ethyl ester

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate
4815-36-5

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate

Conditions
Conditions Yield
With sulfur; diethylamine; In ethanol; for 0.0333333h;
8.4 g
With sulfur; diethylamine; In ethanol; at 20 - 62 ℃; for 1.33333h;
With sulfur; diethylamine; In ethanol; at 20 - 62 ℃; for 1.33h;
195 g
(Z)-2-cyano-3-phenylbut-2-enoic acid ethyl ester
17277-47-3

(Z)-2-cyano-3-phenylbut-2-enoic acid ethyl ester

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate
4815-36-5

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate

Conditions
Conditions Yield
With hydrogen sulfide; In ethanol; ethyl acetate; Petroleum ether;
79%
acetophenone
98-86-2

acetophenone

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate
4815-36-5

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: ammonium acetate; acetic acid / toluene / 18 h / Reflux
2: diethylamine; sulfur / ethanol / 1.33 h / 20 - 62 °C
With ammonium acetate; sulfur; acetic acid; diethylamine; In ethanol; toluene; 1: Knoevenagel Condensation / 2: Gewald reaction;
Multi-step reaction with 2 steps
1: acetic acid / benzene
2: triethylamine; sulfur
With sulfur; acetic acid; triethylamine; In benzene; 1: |Knoevenagel Condensation / 2: |Gewald Aminoheterocycles Synthesis;
Multi-step reaction with 2 steps
1: acetic acid; ammonium acetate / toluene / 18 h / Reflux
2: sulfur; diethylamine / ethanol / 1.33 h / 20 - 62 °C
With ammonium acetate; sulfur; acetic acid; diethylamine; In ethanol; toluene;
Multi-step reaction with 2 steps
1: 3-amino propanoic acid; acetic acid / toluene / 16 h / Reflux; Dean-Stark
2: triethylamine; sulfur / ethanol / 2 h / 50 °C
With sulfur; acetic acid; triethylamine; 3-amino propanoic acid; In ethanol; toluene;
acetophenone
98-86-2

acetophenone

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate
4815-36-5

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 59 percent / acetic acid, ammonium acetate / benzene / Heating
2: 76 percent / sulphur, diethylamine / ethanol / 1.5 h
With ammonium acetate; sulfur; acetic acid; diethylamine; In ethanol; benzene;
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate
4815-36-5

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 59 percent / acetic acid, ammonium acetate / benzene / Heating
2: 76 percent / sulphur, diethylamine / ethanol / 1.5 h
With ammonium acetate; sulfur; acetic acid; diethylamine; In ethanol; benzene;
benzaldehyde
100-52-7

benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate
4815-36-5

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate

Conditions
Conditions Yield
With sulfur; diethylamine; In methanol; ethanol; at 20 ℃; Sonication;
80%
With morpholine; sulfur; at 20 ℃;
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate
4815-36-5

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: ammonium acetate; acetic acid / toluene / 18 h / Reflux
2: diethylamine; sulfur / ethanol / 1.33 h / 20 - 62 °C
With ammonium acetate; sulfur; acetic acid; diethylamine; In ethanol; toluene; 1: Knoevenagel Condensation / 2: Gewald reaction;
Multi-step reaction with 2 steps
1: acetic acid / benzene
2: triethylamine; sulfur
With sulfur; acetic acid; triethylamine; In benzene; 1: |Knoevenagel Condensation / 2: |Gewald Aminoheterocycles Synthesis;
Multi-step reaction with 2 steps
1: acetic acid; ammonium acetate / toluene / 18 h / Reflux
2: sulfur; diethylamine / ethanol / 1.33 h / 20 - 62 °C
With ammonium acetate; sulfur; acetic acid; diethylamine; In ethanol; toluene;
Multi-step reaction with 2 steps
1: 3-amino propanoic acid; acetic acid / toluene / 16 h / Reflux; Dean-Stark
2: triethylamine; sulfur / ethanol / 2 h / 50 °C
With sulfur; acetic acid; triethylamine; 3-amino propanoic acid; In ethanol; toluene;
ethyl 2-amino-4-phenyl-thiophene-3-carboxylate
4815-36-5

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate

Conditions
Conditions Yield
β-Methyl-α-cyan-zimtsaeure-aethylester, Schwefel, w.A., Ggw. von Morpholin, 30-40grad;
1-Morpholino-1-phenyl-aether, S, (C2H5)2NH, 40-50grad;

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