43142-76-3

Usage

Uses

Used in Pharmaceutical Research:
5-CHLORO-3-FORMYL-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER is used as an intermediate in the synthesis of various bioactive molecules for pharmaceutical research. Its potential pharmacological activities, such as anti-inflammatory, antiviral, and antitumor properties, make it a promising candidate for the development of new drug candidates.
Used in Organic Synthesis:
In the field of organic synthesis, 5-CHLORO-3-FORMYL-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER is used as a key building block for the preparation of complex organic compounds. Its unique structure and functional groups allow for versatile chemical reactions, facilitating the synthesis of a wide range of target molecules.
Used in Dye and Pigment Industry:
5-CHLORO-3-FORMYL-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER is used as a precursor in the synthesis of dyes and pigments. Its chemical structure and properties contribute to the development of novel colorants with improved performance characteristics, such as enhanced color strength, stability, and solubility.
Used in Material Science:
In the material science industry, 5-CHLORO-3-FORMYL-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER may be utilized in the development of advanced materials with specific properties. Its potential applications include the synthesis of functional polymers, organic semiconductors, and other materials with tailored characteristics for various applications, such as electronics, sensors, and energy storage devices.

InChI:InChI=1/C12H10ClNO3/c1-2-17-12(16)11-9(6-15)8-5-7(13)3-4-10(8)14-11/h3-6,14H,2H2,1H3

Upstream product

• 4792-67-0 5-chloro-indole-2-carboxylic acid ethyl ester 
• 93-61-8 N-methyl-N-phenylformamide 
• 127-09-3 sodium acetate 
• 107-06-2 1,2-dichloro-ethane 
• 68-12-2 N,N-dimethyl-formamide 
• 5296-86-6 2-[(4-chlorophenyl)-hydrazono]-propionic acid ethyl ester 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 1073-69-4 N-4-chlorophenylhydrazine 

Downstream Products

• 1040379-46-1 C₁₈H₁₃Cl₃N₂O₂ 
• 1040379-43-8 C₁₈H₁₄Cl₂N₂O₂ 
• 1040379-45-0 C₁₉H₁₇ClN₂O₃ 
• 1040379-42-7 C₁₈H₁₅ClN₂O₂ 
• 1040379-49-4 C₁₈H₁₅ClN₂O₃ 
• 1040379-48-3 C₁₉H₁₇ClN₂O₃ 
• 1040379-44-9 C₁₈H₁₄ClFN₂O₂ 
• 16381-47-8 5-chloro-3-methyl-1H-indole-2-carboxylic acid 
• 16382-20-0 5-chloro-3-methyl-1H-indole-2-carboxylic acid ethyl ester 
• 885273-63-2 (E)-3-(5-chloro-2-(ethoxycarbonyl)-1H-indol-3-yl)acrylic acid 
• 380448-07-7 5-chloro-3-formylindole-2-carboxylic acid 

Relevant academic research and scientific papers

Optimization and SAR investigation of novel 2,3-dihydropyrazino[1,2-a]indole-1,4-dione derivatives as EGFR and BRAFV600E dual inhibitors with potent antiproliferative and antioxidant activities

Using a single drug to treat cancer with dual-targeting is an unusual approach when compared to other drug combinations. Dual-targeting agents were developed as a result of insufficient efficacy and drug resistance when single-targeting agents were used.

Design, synthesis, and biological evaluation of novel EGFR inhibitors containing 5-chloro-3-hydroxymethyl-indole-2-carboxamide scaffold with apoptotic antiproliferative activity

New EGFR inhibitor series of fifteen 5-chloro-3-hydroxymethyl-indole-2-carboxamide derivatives has been designed, synthesized, and tested for antiproliferative activity against a panel of cancer cell lines. The results showed that p-substituted phenethyl derivatives 10, 11, 13, 15 and 17–19 showed superior antiproliferative activity compared to their m-substituted counterparts 12, 14, 16 and 20. Compounds 15, 16, 19 and 20 displayed promising EGFR inhibitory activity as well as an increase in caspase 3 levels. Compounds 15 and 19 increased caspase-8 and 9 levels, as well as inducing Bax and decreasing Bcl-2 protein levels. Compound 19 demonstrated cell cycle arrest at pre-G1 and G2/M phases. The results of the docking study into the active site of EGFR revealed strong fitting of the new compounds with higher binding affinities compared to erlotinib.

Design of C3-Alkenyl-Substituted 2-Indolylmethanols for Catalytic Asymmetric Interrupted Nazarov-Type Cyclization

The C3-alkenyl-substituted 2-indolylmethanols have been designed as a new class of substrates for catalytic asymmetric interrupted Nazarov-type cyclizations. In the presence of chiral phosphoric acid as a mild chiral Br?nsted acid, the interrupted Nazarov

Synthesis and biological evaluation of indole-2-carboxamides bearing photoactivatable functionalities as novel allosteric modulators for the cannabinoid CB1 receptor

5-Chloro-3-ethyl-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide (ORG27569, 1) is a prototypical allosteric modulator for the cannabinoid CB1 receptor. Based on this indole-2-carboxamide scaffold, we designed and synthesized novel CB1 allosteric m

Discovery of 3-Substituted 1H-Indole-2-carboxylic Acid Derivatives as a Novel Class of CysLT1 Selective Antagonists

The indole derivative, 3-((E)-3-((3-((E)-2-(7-chloroquinolin-2yl)vinyl)phenyl)amino)-3-oxoprop-1-en-1-yl)-7-methoxy-1H-indole-2-carboxylic acid (17k), was identified as a novel and highly potent and selective CysLT1 antagonist with IC50 values of 0.0059 ± 0.0011 and 15 ± 4 μM for CysLT1 and CysLT2, respectively.

Indole-2-carboxamides as allosteric modulators of the cannabinoid CB 1 receptor

We synthesized new N-phenylethyl-1H-indole-2-carboxamides as the first SAR study of allosteric modulators of the CB1 receptor. The presence of the carboxamide functionality was required in order to obtain a stimulatory effect. The maximum stimulatory activity on CB1 was exerted by carboxamides 13 (EC50 = 50 nM) and 21 (EC50 = 90 nM) bearing a dimethylamino or piperidinyl group, respectively, at position 4 of the phenethyl moiety and a chlorine atom at position 5 of the indole.

Design, synthesis, and SAR of cis-1,2-diaminocyclohexane derivatives as potent factor Xa inhibitors. Part I: Exploration of 5-6 fused rings as alternative S1 moieties

A series of cis-1,2-diaminocyclohexane derivatives were synthesized with the aim of optimizing previously disclosed factor Xa (fXa) inhibitors. The exploration of 5-6 fused rings as alternative S1 moieties resulted in two compounds which demonstrated improved solubility and reduced food effect compared to the clinical candidate, compound A. Herein, we describe the synthesis and structure-activity relationship (SAR), together with the physicochemical properties and pharmacokinetic (PK) profiles of some prospective compounds.

Synthesis and biological activity of functionalized indole-2-carboxylates, triazino- and pyridazino-indoles

Condensation of aryl hydrazines with ethyl pyruvate gave the respective hydrazones 4-6; Fischer indolization led to substituted-1H-indole-2-carboxylic acid ethyl esters 7-9. The Mannich reaction of these compounds with formaldehyde and morpholine yielded ethyl 3-(morpholinomethyl)-substituted-1H-indole-2- carboxylates 10-12. The 5,7-dichloro-1H-indole-2-carbohydrazide 13 was cyclized with methyl orthoformate in DMF to give 6,8-dichloro[1,2,4]triazino[4,5-a]indol- 1(2H)-one 14. Vilsmeier-Haack formylation of 7-9 gave ethyl 3-formyl- substituted-1H-indole-2-carboxylates 15-17 whose 2,2′-((5-chloro-2- (ethoxycarbonyl)-1H-indol-3-yl)methylene)bis-(sulfanediyl) diacetic acid 18 was prepared. The reaction of 15 and 16 with substituted anilines by conventional and microwave methods gave ethyl 3-(N-aryliminomethyl)-5-halo-1H-indole-2- carboxylates 19-29. In a cyclocondensation reaction of 19-25 with thiolactic acid or thioglycolic acid substituted indolylthiazolidinones 30-33 were prepared. Reaction of hydrazine hydrate with 15-17 did not give the respective hydrazones but directly led to the cyclized products substituted-3H- pyridazino[4,5-b]indol-4(5H)-ones 34-36, while a reaction with 2,4-dichlorophenylhydrazine yielded the uncyclized hydrazones. The chlorination of 35 and 36 with POCl3 gave pyridazino[ 4,5-b]indoles 39 and 40, respectively; reaction of the latter compounds with morpholine gave 4-(substituted-5H-pyridazino[4,5-b]indol-4-yl)morpholine 41 and 42. Mannich reaction of 34 with formaldehyde and N-ethylpiperazine gave 8-chloro-3-((4- ethylpiperazin-1-yl)methyl)-3H-pyridazino[ 4,5-b]indol-4(5H)-one 43. The microwave assistance of selected reactions has a profound effect on the reaction speed. The structures of the new compounds were confirmed by both analytical and spectral data. Some compounds were subjected to investigations concerning their antimicrobial, tranquilizing, and anticonvulsant activities.

DIAMINE DERIVATIVES

A compound represented by formula (1):Q1-Q2-To-N(R1) -Q3-N(R2)-T1-Q4 [wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6- membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 represents the following group: (wherein Q5 is an alkylene group having 1 to 8 carbon atoms, or the like); and T0 and T1 are carbonyl groups or the like], a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after artificial valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

Diamine derivatives

A compound represented by the general formula (1): Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4??(1) wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6-membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 is a group in which Q5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T0 and T1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.