乙醛酸乙酯 | 924-44-7

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪醛（含缩醛，半缩醛）
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 乙醛酸乙酯
• 中文别名: 甲酰基甲酸酸乙酯；乙醛酸乙酯溶液；乙醛酸乙酯,甲苯溶液；乙醛酸乙酯50%苯溶液；乙醛酸乙酯(50%甲苯溶液)；2-醛基乙酸乙酯
• 英文名称: ethyl Glyoxylate
• 英文别名: glyoxylic acid ethyl ester；ethyl 2-oxoacetate；ethyl glyoxalate
• CAS: 924-44-7
• 化学式: C₄H₆O₃
• mdl: MFCD00044009
• 分子量: 102.09
• InChiKey: DBPFRRFGLYGEJI-UHFFFAOYSA-N

物化性质

• 沸点：
  110°C
• 密度：
  1.03 g/mL at 20 °C
• 闪点：
  7°C
• 溶解度：
  可溶于氯仿、乙酸乙酯
• 稳定性/保质期：
  在常温常压下，该物质是稳定的。

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• TSCA：
  Yes
• 危险等级：
  3
• 危险品标志：
  Xn,F
• 安全说明：
  S36/37,S62
• 危险类别码：
  R67,R63,R38,R43,R11,R48/20,R65
• WGK Germany：
  3
• 海关编码：
  29183000
• 危险品运输编号：
  UN 1294 3/PG 2
• 危险类别：
  3
• 包装等级：
  II
• 储存条件：
  常温、避光、通风干燥处，密封保存。

SDS

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Section I.Chemical Product and Company Identification
Chemical Name Ethyl Glyoxylate Polymer form (47% in Toluene)
Portland OR
Synonym Ethyl Oxoacetate Polymer form;
Glyoxalic Acid Ethyl Ester Polymer form;
Glyoxylic Acid Ethyl Ester Polymer form
Chemical Formula (CH3CH2OCOCHO)n
924-44-7
CAS Number
108-88-3 (Toluene)

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Section II. Composition and Information on Ingredients
Chemical Name CAS Number Percent (%) TLV/PEL Toxicology Data
Ethyl Glyoxylate Polymer form (47% in Toluene) 924-44-7 ca. 47.0 This compound is classified as (Toluene)
ca. 53.0 a possible mutagen. There is Rat LD50 (oral) 636 mg/kg
108-88-3
no acceptable exposure limit for Rabbit LD50 (dermal) 14100 µL/kg
(Toluene)
a mutagen. Rat LD50 (inhalation) 49 gm/m3/4H

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Section III. Hazards Identification
Acute Health Effects Toxic if ingested or inhaled. Avoid prolonged contact with this material. Overexposure may result in serious illness or death.
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the
eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
Chronic Health Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Reproductive Effects. (Toluene)
Rat TCLo Inhalation 800 mg/m3/6H, female 14-20 days of pregnancy
TOXIC EFFECTS:
Effects on Embryo or Fetus - Fetotoxicity
Effects on Newborn - Behavioral
Mouse TCLo Inhalation 400 ppm/7H, female 7-16 days of pregnancy
TOXIC EFFECTS:
Specific Developmental Abnormalities - Musculoskeletal system
Effects on Newborn - Biochemical and metabolic
MOUSE TDLo Oral 9 gm/kg, female 6-15 days of pregnancy
TOXIC EFFECTS:
Effects on Embryo or Fetus - Fetal death
Repeated exposure to an highly toxic material may produce general deterioration of health by an accumulation in one or
many human organs.

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Section IV. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
minutes. Get medical attention.
Skin Contact In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing
and shoes. Wash clothing before reuse. Thoroughly clean shoes before reuse. Get medical attention immediately.
Inhalation If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
Ingestion INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic
material was ingested; the absence of such signs, however, is not conclusive.
Continued on Next Page
Ethyl Glyoxylate Polymer form (47% in Toluene)

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Section V. Fire and Explosion Data
535°C (995°F) (Toluene)
Flammability Flammable. Auto-Ignition
Flammable Limits LOWER: 1.2% UPPER: 7% (Toluene)
Flash Points 7°C (44.6°F)
4°C (39.2°F) (Toluene)
These products are toxic carbon oxides (CO, CO2).
Combustion Products
Fire Hazards Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media Flammable liquid.
SMALL FIRE: Use DRY chemical powder.
and Instructions
LARGE FIRE: Use alcohol foam, water spray or fog.
Consult with local fire authorities before attempting large scale fire-fighting operations.

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Section VI. Accidental Release Measures
Spill Cleanup Flammable material. Toxic material. Irritating material. Possibly mutagenic material. Air sensitive material.
Keep away from heat. Mechanical exhaust required. Stop leak if without risk. Absorb with DRY earth, sand or other
Instructions
non-combustible material. DO NOT get water inside container. DO NOT touch spilled material. Use water spray to reduce
vapors. Prevent entry into sewers, basements or confined areas; dike if needed. Consult federal, state, and/or local
authorities for assistance on disposal.

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Section VII. Handling and Storage
FLAMMABLE. TOXIC. IRRITANT. POSSIBLE MUTAGEN. AIR SENSITIVE. STORE UNDER ARGON. Keep locked up.
Handling and Storage
Keep away from heat. Mechanical exhaust required. Avoid excessive heat and light. DO NOT ingest. Do not breathe
Information
gas/fumes/ vapor/spray. Wear suitable protective clothing. If ingested, seek medical advice immediately and show the
container or the label. Treat symptomatically and supportively.
Always store away from incompatible compounds such as oxidizing agents.

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Section VIII. Exposure Controls/Personal Protection
Provide exhaust ventilation or other engineering controls to keep the airborne concentrations of vapors below their respective
Engineering Controls
threshold limit value. Ensure that eyewash station and safety shower is proximal to the work-station location.
Splash goggles. Lab coat. Vapor respirator. Boots. Gloves. A MSHA/NIOSH approved respirator must be used to avoid
Personal Protection
inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist BEFORE handling this
product.
Exposure Limits This compound is classified as a possible mutagen. There is no acceptable exposure limit for a mutagen.

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Section IX. Physical and Chemical Properties
Liquid. (Clear, light yellow.) Solubility
Physical state @ 20°C Not available.
1.03
Specific Gravity
0.865 (Toluene)
Molecular Weight (CH3CH2OCOCHO)n Partition Coefficient LOG Kow: 2.73 (Toluene)
C7H8 = 92.14 (Toluene)
Boiling Point 110°C (230°F) Vapor Pressure 3.8 kPa (@ 25°C) (Toluene)
Melting Point -93°C (-135.4°F) (Toluene) Vapor Density 3.1 (Air = 1) (Toluene)
1.48 Not available.
Refractive Index Volatility
1.50 (Toluene)
Critical Temperature Not available. Odor Characteristic.
0.778 cP (@ 0°C) (Toluene) Not available.
Viscosity Taste

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Section X. Stability and Reactivity Data
Stability

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of Instability Avoid excessive heat and light.
Incompatibilities Reactive with oxidizing agents.
Continued on Next Page
Ethyl Glyoxylate Polymer form (47% in Toluene)

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Section XI. Toxicological Information
RTECS Number XS5250000 (Toluene)
Eye Contact. Ingestion. Inhalation.
Routes of Exposure
Toxicity Data (Toluene)
Rat LD50 (oral) 636 mg/kg
Rabbit LD50 (dermal) 14100 µL/kg
Rat LD50 (inhalation) 49 gm/m3/4H
Chronic Toxic Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Reproductive Effects. (Toluene)
Rat TCLo Inhalation 800 mg/m3/6H, female 14-20 days of pregnancy
TOXIC EFFECTS:
Effects on Embryo or Fetus - Fetotoxicity
Effects on Newborn - Behavioral
Mouse TCLo Inhalation 400 ppm/7H, female 7-16 days of pregnancy
TOXIC EFFECTS:
Specific Developmental Abnormalities - Musculoskeletal system
Effects on Newborn - Biochemical and metabolic
MOUSE TDLo Oral 9 gm/kg, female 6-15 days of pregnancy
TOXIC EFFECTS:
Effects on Embryo or Fetus - Fetal death
Repeated exposure to an highly toxic material may produce general deterioration of health by an accumulation in one or many
human organs.
Toxic if ingested or inhaled. Avoid prolonged contact with this material. Overexposure may result in serious illness or death.
Acute Toxic Effects
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the eye
is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.

---

Section XII. Ecological Information
Not available.
Ecotoxicity
Environmental Fate Toluene is released into the atmosphere principally from the volatilization of petroleum fuels and toluene-based solvents and
thinners and from motor vehicle exhaust. Toluene’s production and use as an intermediate in the production of benzoic acid,
benzaldehyde, benzene, explosives, dyes and many other organic compounds may also result in its release to the
environment through various waste streams. Toluene has been detected in emissions from volcanos, forest fires and crude
oil. If released to air, a vapor pressure of 28.4 mm Hg at 25 deg C indicates toluene will exist solely as a vapor in the ambient
atmosphere. Vapor-phase toluene will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl
radicals; the half-life for this reaction in air is estimated to be 3 days. Toluene may also be degraded in the atmosphere by
reaction with nitrate radicals and ozone molecules, but these reactions are too slow to be environmentally important. If
released to soil, toluene is expected to have high to moderate mobility based upon Koc values in the range of 37-178.
Volatilization from moist soil surfaces is expected to be an important fate process based upon a Henry’s Law constant of
6.64X10-3 atm-cu m/mole. Toluene may volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation is
expected to occur rapidly in soil surfaces, with half-lives in the range of several hours to 71 days. If released into water,
toluene is not expected to adsorb to suspended solids and sediment based upon a Koc of 166 measured in lake sediment.
Biodegradation is expected to occur rapidly in water, with reported half-lives of and 56 days in aerobic and anaerobic water,
respectively. Volatilization from water surfaces is expected to be an important fate process based upon this compound’s
Henry’s Law constant. Estimated volatilization half-lives for a model river and model lake are 1 hour and 4 days, respectively.
Measured BCF values of 13 and 90 in fish suggest bioconcentration in aquatic organisms is low to moderate. Hydrolysis is
not expected to be an important environmental fate process for toluene due to lack of hydrolyzable functional groups.
Exposure to toluene may occur occupationally during its production or subsequent use, particularly as a solvent or in gasoline,
via dermal and respiratory routes. The main route of exposure for the general population will be through inhalation from
contaminated air and handling of gasoline as well as ingestion of contaminated drinking water and food, and exposure to
some consumer products.

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Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
Waste Disposal
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.

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Section XIV. Transport Information
DOT CLASS 3: Flammable liquid
DOT Classification
PIN Number
Proper Shipping Name Toluene, solution
Packing Group (PG) II
DOT Pictograms
Continued on Next Page
Ethyl Glyoxylate Polymer form (47% in Toluene)

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This compound is ON the EPA Toxic Substances Control Act (TSCA) inventory list.
(EPA)
WHMIS Classification CLASS B-2: Flammable liquid with a flash point lower than 37.8°C (100°F).
CLASS D-1B: Material causing immediate and serious toxic effects (TOXIC).
(Canada)
On NDSL.
On DSL. (Toluene)
EINECS Number (EEC) 213-105-3
203-625-9 (Toluene)
EEC Risk Statements R11- Highly flammable.
R18- In use, may form flammable/explosive vapor-air mixture.
R23/24/25- Toxic by inhalation, in contact with skin and if swallowed.
R36/37/38- Irritating to eyes, respiratory system and skin.
R46- May cause heritable genetic damage.
R47- May cause birth defects.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学反应

乙醛酸乙酯的分子中具有醛基和酯基，因此能够参与 Diels-Alder 反应、Ene 反应及 Wittig 反应等。

应用

乙醛酸乙酯是有机合成中间体和医药中间体，在实验室研发过程中以及化工医药合成领域都有广泛应用。

合成

将462克乙醇加入421.4克50%的乙醛酸（2.85摩尔）中，然后添加40克（0.406摩尔）浓盐酸。在20分钟内，将混合物加热至55℃。之后，与111克（0.80摩尔）碳酸钾混合。可以通过计算所需中和碳酸钾的量来确定酯化程度，此例中的酯化程度为57.89%。

为了分离形成的碳酸钾，可额外添加400克乙醇以降低其溶解度，随后过滤掉盐。最后，通过蒸馏得到乙醛酸乙酯。合成路线如图所示：

图 乙醛酸乙酯的合成路线

用途

乙醛酸乙酯主要用于有机合成和手性药物的合成。

反应信息

• 作为反应物：
  描述：

  乙醛酸乙酯 在 4-乙酰氨基苯磺酰叠氮 作用下， 生成 重氮乙酸乙酯
  参考文献：
  名称：

  金纳米颗粒催化的α-重氮羰基化合物向碳氢化合物中插入的羧甲基。

  摘要：

  TiO 2上负载的Au纳米颗粒催化α-二重氮羰基化合物中的苯甲酸酯向氢硅烷中的插入。建议该转化涉及两种催化活化方式：通过排出N 2在纳米粒子表面形成亲核金卡宾，以及在金纳米粒子上活化氢硅烷的Si–H键，然后进行化学吸附物质的偶联。不需要外部配体或添加剂，而该过程是纯均相的，因此可以回收和再利用催化剂。

  DOI：

  10.1021/acs.orglett.8b01638
• 作为产物：
  描述：

  草酰氯单乙酯 在 CpRu(PiPr3)(CH3CN)2PF6 、 二甲基苯基硅烷 、 乙腈 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以65%的产率得到乙醛酸乙酯
  参考文献：
  名称：

  二甲基苯基硅烷的化学选择性钌催化将酰基氯还原为醛

  摘要：

  在阳离子钌催化剂{Cp [（i Pr）3 P] Ru（NCMe）2存在下，可以使用二甲基苯基硅烷（HSiMe 2 Ph）作为还原剂将多种芳香族和烷基酰氯选择性地转化为醛类。} + [PF 6 ] -。反应在非常温和的条件下进行，并且可以耐受许多官能团。

  DOI：

  10.1002/adsc.201100693
• 作为试剂：
  描述：

  甲基2-(苯基氨基)乙酸酯 、 乙酰乙酸甲酯 在 乙醛酸乙酯 作用下， 以 乙腈 为溶剂， 反应 40.0h， 以83%的产率得到
  参考文献：
  名称：

  A domino reaction of a β-ketoester, phenylethylamine and ethyl glyoxylate: leading to chiral tricarboxylate containing multiple stereocenters

  摘要：

  A new type of chiral tricarboxylate containing multiple stereocenters was synthesized via the one-pot reaction of a beta-ketoester. (S)-phenylethylamine, and ethyl glyoxylate. High yields and diastereoselectivities (up to 96:4 dr) were obtained under optimal conditions. The reaction of the chiral tricarboxylate with Zn(BH4)(2) gave chiral gamma-lactones in good yields With Lip to 92:8 dr. The structures and configurations of the new chiral tricarboxylates were characterized by X-ray diffraction analysis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.028

文献信息

• Catalytic Enantioselective Synthesis of Bicyclic Lactam <i>N</i> ,<i>S</i> -Acetals in One Pot by Cascade Transformations
  作者：Kaiheng Zhang、Luca Deiana、Erik Svensson Grape、A. Ken Inge、Armando Córdova

  DOI：10.1002/ejoc.201900923

  日期：2019.8.7

  A versatile strategy for the enantioselective synthesis of bicyclic lactam N,S-acetals by one-pot cascade transformations is disclosed. The transformation of readily available substrates is promote ...

  公开了一种通过一锅级联转化对映选择性合成双环内酰胺 N,S-缩醛的通用策略。易于获得的底物的转化促进了...
• Copper-Catalyzed Trifluoromethylation of Aliphatic<i>N</i>-Arylhydrazones: A Concise Synthetic Entry to 2-Trifluoromethylindoles from Simple Aldehydes
  作者：Alexis Prieto、Mélissa Landart、Olivier Baudoin、Nuno Monteiro、Didier Bouyssi

  DOI：10.1002/adsc.201500237

  日期：2015.9.14

  trifluoromethylation of N,N‐disubstituted hydrazones using the Togni reagent is demonstrated to proceed efficiently for aliphatic aldehyde‐derived substrates. The success of the reactions relied on the choice of the N,N‐diphenylamino group as the terminal hydrazone amino group where N,N‐dialkylamino groups were preferred for (hetero)aromatic aldehyde‐derived substrates. In addition, the trifluoromethylated N‐arylhydrazones

  已证明使用Togni试剂对N，N-二取代进行铜催化的C（sp 2）H三氟甲基化可有效地处理脂肪族醛衍生的底物。反应的成功取决于选择N，N-二苯基氨基作为terminal末端基团，其中N，N-二烷基氨基更适合用于（杂）芳醛衍生的底物。此外，三氟甲基化的N-芳基azo烷被证明是费希尔吲哚合成的理想底物，可通过简单的三步法从简单的醛类中获得2-三氟甲基吲哚衍生物。
• [EN] HORMONE RECEPTOR MODULATORS FOR TREATING METABOLIC MUTAGENIC AND FIBROTIC CONDITIONS AND DISORDERS<br/>[FR] MODULATEURS DU RÉCEPTEUR HORMONAL POUR LE TRAITEMENT D'ÉTATS ET DE TROUBLES MÉTABOLIQUES MUTAGÈNES ET FIBROTIQUES
  申请人：ARDELYX INC

  公开号：WO2019055808A1

  公开（公告）日：2019-03-21

  The invention relates to activators of FXR useful in the treatment of autoimmune disorders, liver disease, intestinal disease, kidney disease, cancer, and other diseases in which FXR plays a role, having the Formula (I): wherein L1, A, X1, X2, Y1, Y2, Y3, Y4, R1, R2, and R3 are described herein.

  这项发明涉及FXR的激活剂，可用于治疗自身免疫性疾病、肝病、肠道疾病、肾脏疾病、癌症以及FXR发挥作用的其他疾病，其化学式为（I）：其中L1、A、X1、X2、Y1、Y2、Y3、Y4、R1、R2和R3如本文所述。
• A novel and efficient stereo-controlled synthesis of hexahydroquinolinones via the diene-transmissive hetero-Diels–Alder reaction of cross-conjugated azatrienes with ketenes and electrophilic dienophiles
  作者：Satoru Kobayashi、Tomomi Semba、Taku Takahashi、Satoko Yoshida、Kotaro Dai、Takashi Otani、Takao Saito

  DOI：10.1016/j.tet.2008.10.090

  日期：2009.1

  factors and the electronic demand of the substituents. The second Diels–Alder reaction of the initial [4+2] cycloadducts with electron-deficient dienophiles (TCNE, N-phenylmaleimide) stereoselectively yielded hexahydroquinolinone derivatives. Similarly, a tandem intermolecular–intramolecular mode of the aza-DTHDA reactions produced tetracyclic nitrogen-containing heterocycles in a regio- and stereoselective

  具有N-芳基，N-烷基或N-二甲基氨基取代基的交叉共轭的氮杂三烯（二乙烯基lim或五-1,4-二烯-3-亚胺）的二烯可透过的杂狄尔斯-阿尔德（DTHDA）反应已经进行。检查。氮杂三烯与二苯乙烯酮在室温下的初始反应产生[2 + 2]环加合物的β-内酰胺，在加热后进行[1,3]-σ重排，生成正式的[4 + 2]环加合物。的反应Ñ -phenylazatriene用二甲基乙烯酮或二氯乙烯酮仅产生的[2 + 2] cycloadducts，而反应Ñ-（二甲基氨基）氮杂三烯与二氯乙烯烯不加热得到[4 + 2]环加合物。当[2 + 2]环加合物在β-内酰胺环的C-4具有两个不同的乙烯基取代基时，重排的区域选择性取决于空间因素和取代基的电子需求。最初的[4 + 2]环加合物与缺电子的亲二烯体（TCNE，N-苯基马来酰亚胺）的第二次Diels-Alder反应立体选择性地生成六氢喹啉酮衍生物。同样，氮杂-D
• SYNTHESIS AND USE OF DUAL TYROSYL-DNA PHOSPHODIESTERASE I (TDP1)- TOPOISOMERASE I (TOP1) INHIBITORS
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：US20130345252A1

  公开（公告）日：2013-12-26

  The invention described herein pertains to the synthesis and use of certain N-substituted indenoisoquinoline compounds which inhibit the activity Tyrosyl-DNA Phosphodiesterase I (Tdp1) or Topoisomerase I (Top1) or both, or otherwise demonstrate anticancer activity. Also disclosed are novel N-substituted indenoisoquinoline compounds and pharmaceutical compositions comprising the novel N-substituted indenoisoquinoline compounds.

  本发明涉及合成和使用某些N-取代吲哚异喹啉化合物，这些化合物抑制酪氨酸-DNA磷酸二酯酶I（Tdp1）或拓扑异构酶I（Top1）或两者的活性，或表现出抗癌活性。还公开了新颖的N-取代吲哚异喹啉化合物和包含这些新颖的N-取代吲哚异喹啉化合物的药物组合物。