靛红

靛红用途

【用途一】
用作测定亚酮和噻吩的试剂
【用途二】
用于制还原染料和药物等
【用途三】
该品用作染料和医药的中间体，用于生产药物辛可芬、染料分散黄E-3G；在化学分析中，是测定亚铜离子、硫醇、噻吩、尿蓝母的试剂。
【用途四】
检验亚酮和银的沉淀剂。光度法测定噻吩、硫醇、噻吩、尿蓝姆和浦氨酸的试剂。

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靛红名称

[ CAS 号 ]:
91-56-5

[ 中文名 ]:
吲哚-2,3-二酮

[ 英文名 ]:
isatin

[中文别名 ]:

靛红

[英文别名 ]:

Indolequinone
EINECS 202-077-8
MFCD00005718
indole-2,3-dione
indoline-2,3-dione
Indoquinone
2,3-Dioxoindoline
2,3-Dioxo-2,3-dihydroindole
2,3-Indolinedione
2,3-INDOLEDIONE

靛红生物活性

[ 描述 ]:

Isatin (Indoline-2,3-dione) 是单胺氧化酶 (MAO)的有效抑制剂,IC50 为3 μM。也与中枢苯二氮卓受体结合 (对抗氯硝西泮IC50=123 μM)[1]。还充当心房钠尿肽刺激和一氧化氮刺激的鸟苷酸环化酶拮抗剂[2]。对5-羟色胺系统有影响[3]。

[ 相关类别 ]:

信号通路 >> 神经信号通路 >> 单胺氧化酶

天然产物 >> 生物碱

研究领域 >> 癌症

研究领域 >> 心血管疾病

研究领域 >> 神经疾病

[ 靶点 ]

IC50: 3 μM (MAO B)[1]

[体外研究]

在多巴胺能SH-SY5Y细胞中,靛红(1-400μM)以剂量和时间依赖性方式诱导细胞死亡。这种死亡是生存,凋亡和坏死的连续体[2]。

[体内研究]

单剂量的靛红(80mg/kg)对下丘脑的5-羟色胺能系统具有快速作用。靛红显着增加下丘脑和皮质中的5-HT浓度,但没有显着改变5-HIAA浓度[3]。

[参考文献]

[1]. Glover V, et al. Isatin: Identity with the Purified Endogenous Monoamine Oxidase Inhibitor Tribulin. Journal of Neurochemistry, 51(2), 656–659.

[2]. Igosheva N, et al. Isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells. Neurochem Int. 2005 Aug;47(3):216-24.

[3]. McIntyre IM, et al. Serotonergic effects of isatin: an endogenous MAO inhibitor related to tribulin. J Neural Transm Gen Sect. 1990;79(1-2):35-40.

[相关活性小分子]

靛红物理化学性质

[ 密度 ]:
1.4±0.1 g/cm3

[ 沸点 ]:
360.3±52.0 °C at 760 mmHg

[ 熔点 ]:
193-195 °C (dec.)(lit.)

[ 分子式 ]:
C₈H₅NO₂

[ 分子量 ]:
147.131

[ 闪点 ]:
171.7±30.7 °C

[ 精确质量 ]:
147.032028

[ PSA ]:
46.17000

[ LogP ]:
-0.17

[ 外观性状 ]:
黄色至微红的结晶固体

[ 蒸汽压 ]:
0.0±1.8 mmHg at 25°C

[ 折射率 ]:
1.679

[ 储存条件 ]:
Store at RT.

[ 水溶解性 ]:
水溶性：微溶；可溶于：乙醚

靛红MSDS

靛红毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NL7873000

CHEMICAL NAME :: Indole-2,3-dione

CAS REGISTRY NUMBER :: 91-56-5

BEILSTEIN REFERENCE NO. :: 0383659

LAST UPDATED :: 199701

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C8-H5-N-O2

MOLECULAR WEIGHT :: 147.14

WISWESSER LINE NOTATION :: T56 BMVVJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - changes in motor activity (specific assay)

REFERENCE :: IJPPAZ Indian Journal of Physiology and Pharmacology. (All India Institute of Medical Sciences, Dept. of Physiology, Ansari Nagar, New Delhi 110 029, India) V.1- 1957- Volume(issue)/page/year: 6,145,1962

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 7740 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: GTPZAB Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 27(8),54,1983

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >800 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - changes in motor activity (specific assay)

REFERENCE :: IJPPAZ Indian Journal of Physiology and Pharmacology. (All India Institute of Medical Sciences, Dept. of Physiology, Ansari Nagar, New Delhi 110 029, India) V.1- 1957- Volume(issue)/page/year: 6,145,1962

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 725 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: RPTOAN Russian Pharmacology and Toxicology (English Translation). Translation of FATOAO. (Euromed Pub., 33, Woodlands Rd., Surbiton, Surrey, UK) V.30- 1967- Volume(issue)/page/year: 41,146,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 330 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 55,1514,1959 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 43500 mg/kg/6W-I

TOXIC EFFECTS :: Blood - pigmented or nucleated red blood cells Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in erythrocyte (RBC) count

REFERENCE :: GTPZAB Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 27(3),52,1983 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 200 mg/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - other effects on male

REFERENCE :: IJMRAQ Indian Journal of Medical Research. (Indian Council of Medical Research, Ansari Nagar, New Delhi 110 029, India) V.1- 1913- Volume(issue)/page/year: 67,73,1978 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - A1765 No. of Facilities: 3 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 198 (estimated) No. of Female Employees: 151 (estimated)

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靛红安全信息

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xi,Xn

[ 风险声明 (欧洲) ]:
R36/37/38

[ 安全声明 (欧洲) ]:
S26-S36-S24/25

[ 危险品运输编码 ]:
2811

[ WGK德国 ]:
1

[ RTECS号 ]:
NL7873000

[ 包装等级 ]:
III

[ 危险类别 ]:
6.1(b)

[ 海关编码 ]:
2933990090

靛红合成路线

靛红上下游产品

靛红上游产品

靛红下游产品

靛红制备

【方法一】
先由苯胺三氯乙醛肟缩合制得肟基乙酰苯胺，再经环合，水解制得靛红。

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靛红海关

[ 海关编码 ]: 2933990090

[ 中文概述 ]:
2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

靛红文献

Unprecedented one-pot, domino tertiary alcohol protection-Michael type addition of halides to Morita-Baylis-Hillman adduct of isatin with RCOX/K2CO3: diastereoselective synthesis of oxindole appended β-halo esters.

Org. Lett. 15(6) , 1186-9, (2013)

A facile method utilizing RCOX/K2CO3 as a novel reagent for conjugate addition of hydrogen halide, in addition to tertiary (3°)-hydroxyl protection that leads to the synthesis of functionalized β-halo...

Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators.

J. Med. Chem. 54 , 5320, (2011)

Tryptophan catabolism mediated by indoleamine 2,3-dioxygenase (IDO) is an important mechanism of peripheral immune tolerance contributing to tumoral immune resistance. IDO inhibition is thus an active...

Reactivity of dinuclear copper(II) complexes towards melanoma cells: Correlation with its stability, tyrosinase mimicking and nuclease activity.

J. Inorg. Biochem. 149 , 49-58, (2015)

In this work, the influence of two new dinuclear copper(II) complexes in the viability of melanoma cells (B16F10 and TM1MNG3) was investigated, with the aim of verifying possible correlations between ...

更多文献

靛红

靛红用途

靛红名称

靛红生物活性

靛红物理化学性质

靛红MSDS

详细MSDS(安全技术说明书)

靛红毒性和生态

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

靛红安全信息

靛红合成路线

详细合成路线

靛红上下游产品

靛红上游产品

靛红下游产品

靛红制备

靛红海关

靛红文献

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