靛红

靛红用途

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]。

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 ]:

[ 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)

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

1.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。

2. 将碳酸钠、亚硝酸钠、乙酸、冰和水混匀溶解后，搅拌下通入二氧化硫气体至ph值为1，过程中控制温度不超过10℃。反应结束后，通入蒸汽使温度升至30℃以上。所得羟氨磺酸钠加入三氯乙醛、无水碳钠，充分搅拌至溶解，然后加入苯胺，并通蒸汽，加热至沸2～3min，静置1～1.5h，冷却至结晶完全，过滤、烘干。所得异亚硝基乙酰苯胺分批加入50℃的浓硫酸中，同时，充分搅拌，并用冷水间接冷却，保持温度在60～75℃之间，当异亚硝基乙酰苯胺加完后，升温至80℃，10～15min后，将反应液倒入冷水，静置，结晶完全后，过滤，水洗结晶至中性，所得为粗品。粗品经酸碱沉淀，乙醇重结晶，可得试剂2,3- 二酮茚。过程反应为：

3.制法：

于装有搅拌器、温度计、滴液漏斗的2L反应瓶中，加入靛蓝（2）130g（0.5mol），水400mL，搅拌成均匀悬浊液。加入重铬酸钠175g（0.5mol）溶于200mL水配成的溶液，再加入6.5g硝基苯。冰水浴冷至5℃左右，滴加63%的硫酸285g，控制反应温度0～10℃之间，约7～8h加完^①。放置过夜，而后升温至65℃，反应1.5h。冷至室温，抽滤。弃去水层（绿色），将滤饼加入1300mL水中，加热至50℃，加入氢氧化钠水溶液，至呈碱性。过滤，回收未反应的靛蓝10g。滤液于80℃活性碳脱色后，用盐酸酸化至PH3～4，析出艳橙色结晶。冷却放置24h，抽滤，水洗至中性，100℃干燥，得靛红（1）^②105g，收率77%（按实际参加反应的靛蓝计算），mp199～201℃。注：①加硫酸过程中，反应物从蓝色变为暗棕色。硫酸加完后，反应体系呈酸性。②也可用重铬酸盐在硝酸中氧化靛蓝来制备。

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 ...

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靛红