21743-77-1

Basic information

• Product Name: (2-methyl-2H-tetrazol-5-yl)acetic acid
• CAS NO: 21743-77-1
• Molecular Formula: C₄H₆N₄O₂
• Molecular Weight: 142.116
• Mol File: 21743-77-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 388.5°C at 760 mmHg
• Flash Point: 188.8°C
• Density: 1.63g/cm³
• Vapor Pressure: 9.88E-07mmHg at 25°C
• Refractive Index: 1.686
• CAS DataBase Reference: (2-methyl-2H-tetrazol-5-yl)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2-methyl-2H-tetrazol-5-yl)acetic acid(21743-77-1)
• EPA Substance Registry System: (2-methyl-2H-tetrazol-5-yl)acetic acid(21743-77-1)

Safety Data

• Hazardous Substances Data: 21743-77-1(Hazardous Substances Data)

Usage

Description

(2-methyl-2H-tetrazol-5-yl)acetic acid is a tetrazole derivative, an organic compound characterized by the presence of a tetrazole ring. It is widely recognized for its role as a pharmaceutical intermediate, facilitating the synthesis of a variety of pharmaceutical agents. (2-methyl-2H-tetrazol-5-yl)acetic acid also holds promise due to its potential biological activities and pharmacological properties, making it a significant player in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
(2-methyl-2H-tetrazol-5-yl)acetic acid serves as a crucial pharmaceutical intermediate, utilized in the synthesis of diverse pharmaceutical agents. Its structural properties make it a versatile building block for the development of new medications.
Used in Drug Development:
(2-methyl-2H-tetrazol-5-yl)acetic acid is applied in the research and development of drugs aimed at treating a range of medical conditions. Its potential biological activities and pharmacological properties are under investigation to explore its efficacy and safety in various therapeutic areas.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (2-methyl-2H-tetrazol-5-yl)acetic acid is employed for its capacity to contribute to the design and modification of drug molecules, potentially leading to improved therapeutic options for patients.

Upstream product

• 89488-96-0 ethyl (2-methyl-2H-tetrazol-5-yl)acetate 
• 26476-33-5 (2-methyl-2H-tetrazol-5-yl)-acetic acid methyl ester 

Downstream Products

• 917837-72-0 N-(4-chlorophenyl)-2-methyl-2H-tetrazole-2-acetamide 

Relevant articles and documents

Water-Soluble Platinum(II) Complexes Featuring 2-Alkyl-2H-tetrazol-5-ylacetic Acids: Synthesis, Characterization, and Antiproliferative Activity

2-R-2H-Tetrazol-5-ylacetic acids (abbreviated as 2-R-taa; R = Me, iPr, tBu) react with K2[PtCl4] in 1 m HCl in H2O at r.t. furnishing trans-platinum(II) complexes trans-[PtCl2(2-R-taa)2] (1–3), whereas cis-isomeric species cis-[PtCl2(2-R-taa)2] (R = iPr, 4; tBu, 5) are isolated at lower temperature (4–6 °C). In the presence of EtOH in the reaction mixture, esterification of the tetrazol-5-ylacetoxy group of 2-tBu-taa leads to trans-[PtCl2(ethyl 2-tert-butyl-2H-tetrazol-5-ylacetate)2] (6). Complexes 1–6 were characterized by elemental analyses (CHN), HRESI+-MS,1H,13C{1H},195Pt{1H} NMR and IR spectroscopy, differential scanning calorimetry/thermogravimetry (DSC/TG), and X-ray diffraction (for 1·H2O, 2, 3·2H2O, 4, 5·2H2O, and 6). The generation of the tetrazole-based complexes in solution (1 m DCl in D2O, 25 °C) was studied by1H NMR spectroscopy and HPLC-MS. The obtained data indicate the initial formation of anionic [PtCl3(2-R-taa)]–complexes that are subsequently converted into disubstituted isomeric platinum(II) species cis- and trans-[PtCl2(2-R-taa)2]. By contrast to cis- and trans-[PtCl2(2-R-taa)2] that were inactive in two human cancer models in vitro (IC50> 100 μm), complex 6 demonstrated noticeable antiproliferative effects in HT-29 colon and MCF-7 breast carcinoma cell lines with IC50values of 14.2 ± 1.1 and 5.8 ± 1.2 μm, respectively.

Discovery of Novel TRPM8 Blockers Suitable for the Treatment of Somatic and Ocular Painful Conditions: A Journey through p Kaand LogD Modulation

Transient receptor potential melastatin 8 (TRPM8) is crucially involved in pain modulation and perception, and TRPM8 antagonists have been proposed as potential therapeutic approaches for pain treatment. Previously, we developed two TRPM8 antagonists and proposed them as drug candidates for topical and systemic pain treatment. Here, we describe the design and synthesis of these two TRPM8 antagonists (27 and 45) and the rational approach of modulation/replacement of bioisosteric chemical groups, which allowed us to identify a combination of narrow ranges of pKa and LogD values that were crucial to ultimately optimize their potency and metabolic stability. Following the same approach, we then pursued the development of new TRPM8 antagonists suitable for the topical treatment of ocular painful conditions and identified two new compounds (51 and 59), N-alkoxy amide derivatives, that can permeate across ocular tissue and reduce the behavioral responses induced by the topical ocular menthol challenge in vivo.