214759-22-5

Basic information

• Product Name: (5-CHLOROTHIEN-2-YL)METHYLAMINE
• Synonyms: (5-CHLOROTHIOPHEN-2-YL)METHANAMINE;2-Thiophenemethanamine,5-chloro-(9CI);2-(Aminomethyl)-5-chlorothiophene;5-Chloro-2-thiophenemethanamine;(5-CHLOROTHIEN-2-YL)METHYLAMINE
• CAS NO: 214759-22-5
• Molecular Formula: C₅H₆ClNS
• Molecular Weight: 147.63
• Product Categories: HALIDE
• Mol File: 214759-22-5.mol

Chemical Properties

• Boiling Point: 76-79℃ (3 Torr)
• Flash Point: 81.144 °C
• Appearance: /
• Density: 1.332g/cm³
• Vapor Pressure: 0.191mmHg at 25°C
• Refractive Index: 1.5630 (589.3 nm 20℃)
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 8.39±0.29(Predicted)
• CAS DataBase Reference: (5-CHLOROTHIEN-2-YL)METHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (5-CHLOROTHIEN-2-YL)METHYLAMINE(214759-22-5)
• EPA Substance Registry System: (5-CHLOROTHIEN-2-YL)METHYLAMINE(214759-22-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 214759-22-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Chemistry:
(5-Chlorothien-2-yl)methylamine is used as a key intermediate in the synthesis of various pharmaceutical drugs for its ability to contribute to the development of new therapeutic agents.
Used in Scientific Research and Development:
(5-Chlorothien-2-yl)methylamine is used as a research compound in the field of pharmaceutical chemistry, aiding in the exploration of new drug candidates and potential applications in medicine.
Note: The exact properties like toxicity or potential hazards of (5-Chlorothien-2-yl)methylamine are not widely documented, which necessitates careful handling and usage following strict safety measures.

InChI:InChI=1/C5H6ClNS/c6-5-2-1-4(3-7)8-5/h1-2H,3,7H2

Upstream product

• 96-43-5 2-thienyl chloride 
• 1015434-04-4 C₅H₄N₃SCl 
• 23784-96-5 2-Chloro-5-(chloromethyl)thiophene 
• 27757-85-3 2-Aminomethylthiophene 
• 401485-19-6 tert-butyl N-(thiophen-2-ylmethyl)carbamate 
• 1003-31-2 thiophene-2-carbonitrile 
• 22353-82-8 5-chlorothiophene-2-carboxamide 
• 24065-33-6 5-Chlorothiophene-2-carboxylic acid 
• 42518-98-9 5-chlorothiophene-2-carbonyl chloride 

Downstream Products

• 214755-31-4 N-(5-Chloro-thiophen-2-ylmethyl)-2-(4-fluoro-phenoxy)-nicotinamide 
• 1018480-83-5 C₁₇H₁₃ClF₃N₃O₂S₂ 
• 438208-71-0 {[(5-chloro(2-thienyl))methyl]amino}-N-[4-(5-chloro-1,3-dioxobenzo[c]azolidin-2-yl)-3-methylphenyl]carboxamide 
• 1123819-36-2 C₂₇H₁₇ClF₃N₃O₂S 
• 1123819-16-8 C₂₆H₁₇ClF₃N₃O₂S 
• 1123819-09-9 C₂₅H₁₇Cl₂N₃O₂S 
• 1123818-87-0 C₂₅H₁₈ClN₃O₂S 

Relevant articles and documents

COMPOUNDS FOR USE IN PREVENTION AND TREATMENT OF NEURODEGENERATIVE DISEASES AND PAIN

Compounds for use in prevention and treatment of neurodegenerative disease and pain are disclosed. In one embodiment of the invention, the compound is selected from the group consisting of N6-[(3-halothien-2-yl)methyl]adenosine, N6-[(4-halothien-2-yl)methyl]adenosine, and N6-[(5-halothien-2-yl)methyl]adenosine. In another embodiment of the invention, the compound is selected from the group consisting of N6-[(2-bromothien-3-yl)methyl]adenosine, N6-[(4-bromothien-3-yl)methyl]adenosine, N6-[(5-bromothien-3-yl)methyl]adenosine N6-[(2-chlorothien-3-yl)methyl]adenosine, N6-[(4-chlorothien-3-yl)methyl]adenosine, and N6-[(5-chlorothien-3-yl)methyl]adenosine. Also disclosed are methods of making and using the same.

Novel quinazoline EGFR inhibitor, and preparation method and application thereof

A novel quinazoline EGFR inhibitor, and a preparation and an application thereof belong to the field of synthesis of medicines. The novel quinazoline EGFR inhibitor has a general formula shown in thedescription; and in the general formula, R is one from H, F, Cl, Br, and I, and R1 and R2 are same to or different from each other, and are respectively selected from H, a nitro group, an amino group,a hydroxyl group, a 2-methoxyethoxy group, a C1-C4 alkoxy group and a C1-C4 alkyl group. The novel quinazoline EGFR inhibitor is different from existing quinazoline inhibitors with the 4-position substituted with various anilines, and is designed and synthesized by substituting the 4-position of a quinazoline skeleton with a broadly bioactive thienylmethylamine and reasonably modifying the 6-position and the 7-position with groups not including an electrophilic acrylamide bond in order to avoid covalent bonds with EGFR. Compared with existing antitumor drugs, the above compound can significantly inhibit EGFR phosphorylation, and has excellent anti-proliferative activity against EGFR overexpressing tumor cells (such as A431 and MCF-7).

Design and synthesis of heteroaromatic-based benzenesulfonamide derivatives as potent inhibitors of H5N1 influenza A virus

Influenza A virus is an enveloped negative single-stranded RNA virus that causes febrile respiratory infection and represents a clinically challenging threat to human health and even lives worldwide. Even more alarming is the emergence of highly pathogenic avian influenza (HPAI) strains such as H5N1, which possess much higher mortality rate (60%) than seasonal influenza strains in human infection. In this study, a novel series of heteroaromatic-based benzenesulfonamide derivatives were identified as M2 proton channel inhibitors. A systematic investigation of the structure-activity relationships and a molecular docking study demonstrated that the sulfonamide moiety and 2,5-dimethyl-substituted thiophene as the core structure played significant roles in the anti-influenza activity. Among the derivatives, compound 11k exhibited excellent antiviral activity against H5N1 virus with an EC50 value of 0.47 μM and selectivity index of 119.9, which are comparable to those of the reference drug amantadine.

COMPOUNDS FOR USE IN PREVENTION AND TREATMENT OF NEURODEGENERATIVE DISEASES AND PAIN

Compounds for use in prevention and treatment of neurodegenerative disease and pain are disclosed. In one embodiment of the invention, the compound is selected from the group consisting ofN 6 -[(3-halothien-2-yl)methyl]adenosine,N 6 -[(4-halothien-2-yl)methyl]adenosine, andN 6 -[(5-halothien-2-yl)methyl]adenosine. In another embodiment of the invention, the compound is selected from the group consisting ofN 6 -[(2-bromothien-3-yl)methyl]adenosine,N 6 -[(4-bromothien-3-yl)methyl]adenosine,N 6 -[(5-bromothien-3-yl)methyl]adenosineN 6 -[(2-chlorothien-3-yl)methyl]adenosine,N 6 -[(4-chlorothien-3-yl)methyl]adenosine, andN 6 -[(5-chlorothien-3-yl)methyl]adenosine. Also disclosed are methods of making and using the same.

Synthesis and biological evaluation of some novel thiophene-bearing quinazoline derivatives as EGFR inhibitors

Background: With the approval of gefitinib, erlotinib, afatinib, and osimertinib for clinical use, targeting Epidermal Growth Factor Receptor (EGFR) has been intensively pursued. Similar to most therapies, challenges related to the treatment resistance against these drugs have emerged over time, so new EGFR Tyrosine Kinase Inhibitors (TKIs) need to be developed. This study aimed to investigate the potential use of a series of thiophene-bearing quinazoline derivatives as EGFR inhibitors. We designed and synthesized nine quinazolin derivatives, among which five compounds (5e, 5f, 5g, 5h, and 5i) were reported for the first time. Methods: Two cancer cell lines, A431 (overexpressing EGFR) and A549 (EGFR wild-type and K-ras mutation), were treated by these compounds and subjected to MTT assay. The A431 cells were selected for further treatment (5e) and Western blot analysis. Results: Although the compounds exerted no obvious effects on the proliferation of A549 cells, seven out of the nine compounds significantly inhibited the growth of A431 cells. In particular, the IC50 values of 5e and erlotinib were nearly equal. Western blot results showed that 5e significantly inhibited EGFR autophosphorylation in A431 cells. Structure-activity relationships indicated that quinazolines bearing 6,7-side chains were more potent than those unsubstituted at the 6,7-positions. Moreover, electron-withdrawing hydrophobic groups on the 5-position of the thiophene were preferred, such as chlorine or bromine atom. Conclusion: Nine 4-aminoquinazolin derivatives were designed, synthesized, and evaluated against A431 and A549 cell lines. Seven compounds significantly inhibited the growth of A431 cells. In particular, 5e possessed similar antitumor potency to that of erlotinib.

Systematic structure-activity relationship (SAR) exploration of diarylmethane backbone and discovery of a highly potent novel uric acid transporter 1 (URAT1) inhibitor

In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a-1x and 1ha-1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly potent novel URAT1 inhibitor, 1h, which was 200-and 8-fold more potent than parent lesinurad and benzbromarone, respectively (IC50 = 0.035 μM against human URAT1 for 1h vs. 7.18 μM and 0.28 μM for lesinurad and benzbromarone, respectively). Compound 1h is the most potent URAT1 inhibitor discovered in our laboratories so far and also comparable to the most potent ones currently under development in clinical trials. The present study demonstrates that the diarylmethane backbone represents a very promising molecular scaffold for the design of potent URAT1 inhibitors.

Development of Glucose Regulated Protein 94-Selective Inhibitors Based on the BnIm and Radamide Scaffold

Glucose regulated protein 94 (Grp94) is the endoplasmic reticulum resident of the heat shock protein 90 kDa (Hsp90) family of molecular chaperones. Grp94 associates with many proteins involved in cell adhesion and signaling, including integrins, Toll-like receptors, immunoglobulins, and mutant myocilin. Grp94 has been implicated as a target for several therapeutic areas including glaucoma, cancer metastasis, and multiple myeloma. While 85% identical to other Hsp90 isoforms, the N-terminal ATP-binding site of Grp94 possesses a unique hydrophobic pocket that was used to design isoform-selective inhibitors. Incorporation of a cis-amide bioisostere into the radamide scaffold led to development of the original Grp94-selective inhibitor, BnIm. Structure-activity relationship studies have now been performed on the aryl side chain of BnIm, which resulted in improved analogues that exhibit better potency and selectivity for Grp94. These analogues also manifest superior antimigratory activity in a metastasis model as well as enhanced mutant myocilin degradation in a glaucoma model compared to BnIm.

PLATELET ADP RECEPTOR INHIBITORS

no abstract published

COMPOUNDS FOR USE IN PREVENTION AND TREATMENT OF NEURODEGENERATIVE DISEASES AND PAIN

Compounds for use in prevention and treatment of neurodegenerative disease and pain are disclosed. In one embodiment of the invention, the compound is selected from the group consisting of N66-[(3-halothien-2-yl)methyl]adenosine, N66-[(4-halothien-2-yl)methyl]adenosine, and N66-[(5-halothien-2-yl)methyl]adenosine. In another embodiment of the invention, the compound is selected from the group consisting of N66-[(2-bromothien-3-yl)methyl]adenosine, N66-[(4-bromothien-3-yl)methyl]adenosine, N66-[(5-bromothien-3-yl)methyl]adenosine N66-[(2-chlorothien-3-yl)methyl]adenosine, N66-[(4-chlorothien-3-yl)methyl]adenosine, and N66-[(5-chlorothien-3-yl)methyl]adenosine. Also disclosed are methods of making and using the same.

PLATELET ADP RECEPTOR INHIBITORS

Compounds are provided which are useful as platelet ADP receptor inhibitors, for treating thrombosis and for reducing the likelihood and/or severity of a secondary ischemic event in a patient.