이미다졸

이미다졸 속성

이미다졸 C화학적 특성, 용도, 생산

물성

글리옥살에 폼알데하이드와 암모니아를 반응시켜 얻는, 무색 고체. 강한 염기성을 띠며, 물, 알코올에 잘 녹는다. 화학식은 C3H4N2. [비슷한 말] 글리옥살린.

개요

Imidazole group denotes a heterocyclic organic compound whose molecule contains a five-membered hetero-aromatic ring of two non-adjacent nitrogen atoms, that a carbon atom is placed between two nitrogen atoms. Imidazole is the universally used trivial name for 1,3-azole. Earlier given names were glyoxaline and iminazole. The importance of this aromatic ring system is reflected by its presence in naturally occurring histidine, histamine and the purines, and in several classes of pharmaceuticals. Imidazole can act as a base and as a weak acid. It exists in two tautomeric forms with the hydrogen atom taking position between the two nitrogen atoms.

화학적 성질

Imidazole is a moderately strong base (pKb= 7.0), and a weak acid (pKa= 14.9). Imidazoles substituted with electron-withdrawing groups are stronger acids than imidazole itself; e.g., 4(5)-nitroimidazole has a pKa of 9.3. Imidazole is stable at 400°C, possesses considerable aromatic character, and undergoes the usual electrophilic aromatic substitution reactions. Nitration and sulfonation require, however, far more drastic conditions than the corresponding reactions with benzene. Other substitution reactions of imidazole include halogenation, hydroxymethylation, coupling with aromatic diazonium salts, and carboxylation.

역사

Imidazole[288-32-4] was first synthesized in 1858 by Debus from ammonia and glyoxal; it was originally named glyoxalin. The name imidazole was introduced by Hantzsch. Industrial production of imidazole began in the 1950s; a wide range of derivatives is now available in industrial quantities.

주요 응용

Imidazole is a versatile heterocycle used in the preparation of various biologically active compounds such as the amino acid histidine and is present in many antifungal medication. It is also used ext ensively as a corrosion inhibitor on transition metals such as copper.It is used in organic synthesis and as an antiirradiationagent.
Imidazole has been used:
in the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein.
in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography.
as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cell.

제조 방법

Imidazole is formed by reacting glyoxal with formaldehyde in the presence of ammonium acetate in acetic acid. The driving energy is microwave radiation. More generally, this reaction is used to produce substituted imidazoles.

Although there had been discoveries of various derivatives of imidazole in 1840, it was first reported in 1858. The synthesis process of imidazole follows the reaction between formaldehyde in ammonia and glyoxal. This process gives low yield of imidazole but it is still used to form imidazole with C-substitution (Wolkenberg et al., 2004).

정의

ChEBI: Imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. It is an important pharmacophore in drug discovery. Imidazole is used as a Karl Fischer reagent in analytical chemistry and a reagent in synthetic organic chemistry.

일반 설명

Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.

건강위험

It is less toxic relative to pyrrole and otherfive-membered heterocyclic compounds ofnitrogen. Intraperitoneal administration ofimidazole caused somnolence, muscle contractions,and convulsions in mice. Theoral LD50 value in mice is in the range900 mg/kg.

화재위험

Noncombustible solid.

Mechanism of action

N-substitution of imidazoles has created a family of drugs, called triazoles, that have the same mechanism of action as imidazoles, a similar or broader spectrum of activity, and less effect on human sterol synthesis. Both imidazoles and triazoles inhibit C-14α demethylation of lanosterol in fungi by binding to one of the cytochrome P-450 enzymes, which leads to the accumulation of C-14α methylsterols and reduced concentrations of ergosterol, a sterol essential for a normal fungal cytoplasmic membrane. Inhibition of cytochrome P-450 also decreases the synthesis of testosterone and glucocorticoids in mammals, an effect seen clinically with ketoconazole but not with later azoles[1].

Purification Methods

Crystallise imidazole from *benzene, CCl4, CH2Cl2, EtOH, pet ether, acetone/pet ether and distilled de-ionized water. Dry it at 40o under vacuum over P2O5. Distil it at low pressure. It is also purified by sublimation or by zone melting. [Snyder et al. Org Synth Coll Vol III 471 1955, Bredereck et al. Chem Ber 97 827 1964, Caswell & Spiro J Am Chem Soc 108 6470 1986.] 15N-imidazole crystallises from *benzene [Scholes et al. J Am Chem Soc 108 1660 1986]. [Beilstein 23 II 34, 23 III/IV 564, 23/4 V 191.]

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이미다졸 공급 업체

공급자	전화	이메일	국가	제품 수	이점
Aladdin Scientific		tp@aladdinsci.com	United States	57505	58
Anhui Royal Chemical Co., Ltd.	+86-25-86655873 +8613962173137	marketing@royal-chem.com	China	193	55
Shandong Believe Chemical PTE.LTD	+86-18553607090 +8618553607090	1093908296@qq.com	China	1667	58
Hebei Chuanghai Biotechnology Co,.LTD	+86-13131129325	sales1@chuanghaibio.com	China	5878	58
Hefei TNJ Chemical Industry Co.,Ltd.	+86-0551-65418671 +8618949823763	sales@tnjchem.com	China	34563	58
Hebei Yanxi Chemical Co., Ltd.	+8617531153977	allison@yan-xi.com	China	5855	58
Wuhan Quanjinci New Material Co.,Ltd.	+86-15271838296; +8615271838296	kyra@quanjinci.com	China	1512	58
Aladdin Scientific		tp@aladdinsci.com	United States	52924	58
Shandong Dexiang International Trade Co., Ltd	+86-15662691337 +86-15662695772	539942812@qq.com	China	998	58
Yancheng Green Chemicals Co.,Ltd	+undefined-86-25-86655873	info@royal-chem.com	China	114	58

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