CAS: 3471-31-6; 2-(5-Methoxy-1H-Indol-3-yl)Acetic Acid

该化合物是一种化学化合物,属于非甲醚衍生物类别,其特点是在异戊醇环的5处放置有甲氧基(-OCH3),并有乙酸乙酸基酸酸酸,这助长了其酸性能;该化合物因其潜在的生物活动而闻名,包括其作为植物生长调节器的作用及其参与各种生理过程的情况;该化合物在有机溶剂中表现出溶解性,这种溶解性是非甲醚衍生物的典型特征,而其在水中的溶性可能因pH而异.该化合物的结构允许与生物系统互动,使其既对农业和制药研究感兴趣.此外,5-甲基催产素乙酸可参与各种化学反应,包括进化和恐吓,因为有箱酸功能组的存在,其独特的特性和潜在应用使其成为生物化学和医药化学领域的研究对象.

英文名称2-(5-Methoxy-1H-Indol-3-yl)Acetic Acid
中文名称5-甲氧基吲哚-3-乙酸
IUPAC名称2-(5-methoxy-1H-indol-3-yl)acetic acid
其它别名5-Methoxy-3-indoleacetic acid
CAS编号3471-31-6
MFCD编号:MFCD00005638
EINECS号:222-438-3
FDA UNII编号:MSN7CK6ETH
分子式:C11H11NO3
分子量:205.21
产品CID: 1351262
产品分类有机原料→分子砌块→芳杂环类化合物→吲哚类化合物

相似结构搜索
InChIKey: COCNDHOPIHDTHK-UHFFFAOYSA-N
InChI=1S/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14)…
计算化学: 氢键受体数2.0氢键供体数2.0可旋转键数3.0

MSDS等安全信息

GHS象形图
GHS符号GHS07;
注释: Exclamation mark
危险类别急性毒性类别4(吸入)
急性毒性类别4(经皮)
急性毒性类别4(经口)
特定目标器官毒性 - 单次接触类别3
皮肤腐蚀/刺激类别2
严重眼刺激类别2A
警示词Warning(警告)
危险描述H332 |吸入有害.
H312 |皮肤接触有害.
H302 |吞咽有害.
H335 |可能引起呼吸道刺激.
H315 |造成皮肤刺激.
H319 |造成严重眼刺激.
防范说明P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
UN编号NONH for all modes of transport
危险品标志Xi
安全声明24/25
WGK Germany3

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

合成工艺路线路线简述

3-(Carboxymethyl)-5-Methoxy-1H-Indole-2-Carboxylic Acid置于盐酸,Copper Chromite,Sodium Hydroxide体系中,用喹啉,乙醇作为反应溶剂,化学反应 4.5H,反应生成 5-甲氧基吲哚-3-乙酸
参考文献:新的n-(吡啶-4-基)-(吲哚-3-基)乙酰胺和丙酰胺作为抗过敏剂.
标题:新的n-(吡啶-4-基)-(吲哚-3-基)乙酰胺和丙酰胺作为抗过敏剂.
摘要:为了寻找新的抗过敏化合物,已经制备了一系列新的n-(吡啶-4-基)-(吲哚-3-基)烷基酰胺44-84.通过在fischer条件下进行吲哚化来合成所需的(2-甲基吲哚-3-基)乙酸乙酯1-4.japp-Klingemann方法,然后进行2-脱羧,得到(吲哚-3-基)链烷酸乙酯17-25.通过使相应的酸或其n-芳基(甲基)衍生物与2-氯-1-甲基吡啶碘化物促进的4-氨基吡啶缩合而成功进行了酰胺化反应.通过改变吲哚取代基(r1,R2,R)和烷链长度(n = 1,2,3)来改善标题系列的抗过敏效力的努力导致选择n-(吡啶-4 41种化合物中的45-基)-[1-(4-氟苄基)吲哚-3-基]乙酰胺45.使用豚鼠腹膜肥大细胞,在卵白蛋白诱导的组胺释放测定中,该酰胺的效价比阿司咪唑高406倍,Ic50 = 0.016 Microm.在th-2细胞的il-4产生测试中,其抑制活性与参考组胺拮抗剂的抑制活性相同(ic50
DOI:10.1021/jm981079+

海关参考信息

2912110000-甲醛
2912120000-乙醛
2915110000-甲酸
2915211900-乙酸
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-7816375-B2
优先权日:2000-09-11
标题 :Ligands for monoamine receptors and transporters, and methods of use thereof
发明人：AQUILA BRIAN M; BANNISTER THOMAS D; CUNY GREGORY D; HAUSKE JAMES R; HOLLAND JOANNE M; PERSONS PAUL E; RADEKE HEIKE; WANG FENGJIANG; SHAO LIMING
权利人:SEPRACOR INC
摘要:One aspect of the present invention relates to heterocyclic compounds. A second aspect of the present invention relates to the use of the heterocyclic compounds as ligands for various mammalian cellular receptors, including dopamine, serotonin, or norepinephrine transporters. The compounds of the present invention will find use in the treatment of numerous ailments, conditions and diseases which afflict mammals, including but not limited to addiction, anxiety, depression, sexual dysfunction, hypertension, migraine, Alzheimer's disease, obesity, emesis, psychosis, schizophrenia, Parkinson's disease, inflammatory pain, neuropathic pain, Lesche-Nyhane disease, Wilson's disease, and Tourette's syndrome. An additional aspect of the present invention relates to the synthesis of combinatorial libraries of the heterocyclic compounds, and the screening of those libraries for biological activity, e.g., in assays based on dopamine transporters.

专利号:US-2024217929-A1
优先权日:2019-11-07
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专利号:US-12084417-B2
优先权日:2019-11-07
标题:Synthesis of N,N-dimethyltryptamine-type compounds, methods, and uses

专利号:US-11643390-B2
优先权日:2019-11-07
标题:Synthesis of N,N-dimethyltryptamine-type compounds, methods, and uses

专利号:US-2023250059-A1
优先权日:2019-11-07
标题:Synthesis of n,n-dimethyltryptamine-type compounds, methods, and uses

专利号:US-2021395201-A1
优先权日:2019-11-07
标题 :Synthesis of n,n-dimethyltryptamine-type compounds, methods, and uses

其他信息查阅

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主要参考文献

[参考文献]: Kveder S, Et Al. The Metabolism Of Melatonin (N-Acetyl-5-Methoxytryptamine) And 5-Methoxytryptamine. J Biol Chem. 1961 Dec;236:3214-20.
[参考文献]: C Bertolucci, Et Al. Photoperiod Affects Amplitude But Not Duration Of In Vitro Melatonin Production In The Ruin Lizard (Podarcis Sicula). J Biol Rhythms. 2003 Feb;18(1):63-70.
[参考文献]: J Yáez, Et Al. Secretion Of Methoxyindoles From Trout Pineal Organs In Vitro: Indication For A Paracrine Melatonin Feedback. Neurochem Int. 1995 Aug;27(2):195-200.
[参考文献]: J Yáez, Et Al. Secretion Of The Methoxyindoles Melatonin, 5-Methoxytryptophol, 5-Methoxyindoleacetic Acid, And 5-Methoxytryptamine From Trout Pineal Organs In Superfusion Culture: Effects Of Light Intensity. Gen Comp Endocrinol. 1996 Feb;101(2):165-72.
[参考文献]: M S Grace, Et Al. Melatonin Deacetylase Activity In The Pineal Gland And Brain Of The Lizards Anolis Carolinensis And Sceloporus Jarrovi. Neuroscience. 1994 Sep;62(2):615-23.

合成参考文献

摘要:Journal of Toxicology and Environmental Health., 1(515), 1976 []
参考文献:10.1016/0306-4522(94)90393-x
摘要:Grace MS, Besharse JC. Melatonin deacetylase activity in the pineal gland and brain of the lizards Anolis carolinensis and Sceloporus jarrovi. Neuroscience. 1994 Sep;62(2):615–23. doi: 10.1016/0306-4522(94)90393-x.
参考文献:10.1002/jssc.200500095
摘要:Pobozy E, Michalski A, Sotowska-Brochocka J, Trojanowicz M. Determination of melatonin and its precursors and metabolites using capillary electrophoresis with UV and fluorometric detection. J Sep Sci. 2005 Nov;28(16):2165–72. doi: 10.1002/jssc.200500095.

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