2,3-二氧吲哚林-7-羧酸 | 25128-35-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 2,3-二氧吲哚林-7-羧酸
• 中文别名: 2,3-吲哚醌-7-羧酸；2,3-二氧代-7-吲哚啉羧酸；7-靛红甲酸
• 英文名称: isatin-7-carboxylic acid
• 英文别名: 2,3-dioxoindoline-7-carboxylic acid；1H-indole-2,3-dione-7-carboxylic acid；2,3-dioxo-1H-indole-7-carboxylic acid
• CAS: 25128-35-2
• 化学式: C₉H₅NO₄
• mdl: MFCD00612492
• 分子量: 191.143
• InChiKey: ROODQCZSWXEDJL-UHFFFAOYSA-N

物化性质

• 熔点：
  268 °C
• 密度：
  1.591±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 安全说明：
  S26,S37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Name:	2 3-Dioxoindoline-7-carboxylic acid tech Material Safety Data Sheet
Synonym:
CAS:	25128-35-2

Section 1 - Chemical Product MSDS Name:2 3-Dioxoindoline-7-carboxylic acid tech Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
25128-35-2	2,3-Dioxoindoline-7-carboxylic acid		unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 25128-35-2: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 275 - 276 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H5NO4
Molecular Weight: 191

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents, bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 25128-35-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,3-Dioxoindoline-7-carboxylic acid - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 25128-35-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 25128-35-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 25128-35-2 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

合成方法 步骤一：2,3-二氧吲哚林-7-甲腈的合成

在100ml三颈瓶中加入2,3-二氧吲哚林-7-甲醛、盐酸羟胺、乙酸钠、30mL冰醋酸和1mL醋酐，并安装搅拌器、温度计和回流冷凝管。进行回流反应后，冷却并倒入冰水中，析出固体，过滤、水洗后烘干，最终通过重结晶获得2,3-二氧吲哚林-7-甲腈。

步骤二：2,3-二氧吲哚林-7-甲酸的合成

在100ml三颈瓶中加入2,3-二氧吲哚林-7-甲腈、NaOH和水，并安装搅拌器、温度计和回流冷凝管。进行回流反应后，冷却并过滤滤液，用稀盐酸酸化至pH<3，析出固体，过滤烘干以获得化合物2,3-二氧吲哚林-7-羧酸。

反应信息

• 作为反应物：
  描述：

  2,3-二氧吲哚林-7-羧酸 在 sodium hydroxide 、 硫酸 作用下， 生成 3-hydroxy-2-phenyl-quinoline-4,8-dicarboxylic acid dipropyl ester
  参考文献：
  名称：

  SOME ALKYL ESTER AND CARBAMATE DERIVATIVES OF 3-HYDROXY-2-PHENYLQUINOLINE

  摘要：

  DOI：

  10.1021/jo01365a001
• 作为产物：
  描述：

  2-(2-hydroxyimino-acetylamino)-benzoic acid 在 硫酸 作用下， 生成 2,3-二氧吲哚林-7-羧酸
  参考文献：
  名称：

  Sandmeyer, Helvetica Chimica Acta, 1919, vol. 2, p. 239

  摘要：

  DOI：
• 作为试剂：
  描述：

  2,3-二氧吲哚林-7-羧酸 在 sodium hydroxide 、 2,3-二氧吲哚林-7-羧酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.75h， 生成
  参考文献：
  名称：

  稠合四环喹啉和喹喔啉的N- [2-（二甲基氨基）乙基]羧酰胺衍生物的合成及其抗肿瘤特性：一类新型的拓扑异构酶抑制剂。

  摘要：

  制备了一系列四环喹啉和喹喔啉羧酰胺，并在一系列鼠类人肿瘤细胞系中评估了它们的细胞毒性。多数喹啉衍生物是通过适应Pfitzinger合成，随后进行热脱羧并使用氯甲酸异丁酯通过混合酸酐法与N，N-二甲基乙二胺偶联而制备的。喹啉类似物显示出与已知的三环a啶-4-羧酰胺混合的topoI / II抑制剂DACA相似的细胞毒性，其中噻吩和茚满类似物最具活性。他们显示出对Jurkat人白血病topo II耐药株JLA和JLC的效力几乎没有降低，表明它们的细胞毒性并非主要是由于对topo II的抑制所致。喹喔啉类似物的IC50值变化更大，与喹啉衍生物相比，其平均细胞毒性要低，但似乎具有相似的作用方式。总的来说，这类新化合物似乎是混合的topo I / II抑制剂，在研究的人类白血病细胞系中的细胞毒性比DACA高三倍，在结肠38的体内活性与DACA和阿霉素相当。

  DOI：

  10.1021/jm970044r

文献信息

• Synthesis and Biological Evaluation of Quinoline Salicylic Acids As P-Selectin Antagonists
  作者：Neelu Kaila、Kristin Janz、Silvano DeBernardo、Patricia W. Bedard、Raymond T. Camphausen、Steve Tam、Desirée H. H. Tsao、James C. Keith、Cheryl Nickerson-Nutter、Adam Shilling、Ruth Young-Sciame、Qin Wang

  DOI：10.1021/jm0602256

  日期：2007.1.1

  junctions into the underlying tissue. The initial rolling step is mediated by the interaction of leukocyte glycoproteins containing active moieties such as sialyl Lewisx (sLex) with P-selectin expressed on endothelial cells. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of inflammatory diseases such as arthritis

  白细胞炎症和组织损伤部位的募集涉及白细胞沿内皮壁滚动，然后白细胞牢固粘附，最后白细胞跨细胞连接转运到下面的组织中。初始滚动步骤由包含活性部分的白细胞糖蛋白（如唾液酸化的Lewisx（sLex））与在内皮细胞上表达的P-选择蛋白的相互作用介导。因此，借助于小分子P-选择蛋白拮抗剂抑制这种相互作用是治疗炎性疾病如关节炎的有吸引力的策略。惠氏化学文库的高通量筛选确定了喹啉水杨酸类化合物（1）作为P-选择素的拮抗剂，其体外和基于细胞的测定方法的功效远远优于sLex。通过迭代药物化学，我们鉴定出具有改善的P-选择素活性，减少的二氢Orate脱氢酶抑制作用和可接受的CYP谱的类似物。铅化合物36在类风湿关节炎的大鼠AIA模型中有效。
• Bisintercalating Threading Diacridines:  Relationships between DNA Binding, Cytotoxicity, and Cell Cycle Arrest
  作者：Laurence P. G. Wakelin、Xianyong Bu、Alexandra Eleftheriou、Alpesh Parmar、Charbel Hayek、Bernard W. Stewart

  DOI：10.1021/jm030253d

  日期：2003.12.1

  synthesized a series of bis(9-aminoacridine-4-carboxamides) linked via the 9-position with neutral flexible alkyl chains, charged flexible polyamine chains, and a semirigid charged piperazine-containing chain. The carboxamide side chains comprise N,N-dimethylaminoethyl and ethylmorpholino groups. The compounds are designed to bisintercalate into DNA by a threading mode, in which the side chains are intended to

  我们已经合成了一系列经由9位与中性柔性烷基链，带电柔性多胺链和半刚性带电含哌嗪的双（9-氨基ac啶-4-甲酰胺）连接。羧酰胺侧链包含N，N-二甲基氨基乙基和乙基吗啉代基团。这些化合物设计为通过穿线方式双插入DNA，在这种方式中，侧链旨在与主沟中鸟嘌呤的O6 / N7原子形成氢键接触，连接子位于次沟中。通过这种方式，我们预计它们将与DNA缓慢解离，并且由于模板抑制转录而具有细胞毒性。二聚体以26至46度的螺旋展开角去除并逆转了封闭的环状DNA的超螺旋，证实了在所有情况下的双功能嵌入，并且代表性成员的DNA复合物的解离速度比简单的氨基slowly啶要慢许多数量级。确定了对人类白血病CCRF-CEM细胞的细胞毒性，最具活性的药物的IC（50）值为35-50 nM，范围超过20倍，而二甲基氨基乙基和乙基吗啉代系列在本质上都没有毒性。与已建立的转录抑制剂一样，吗啉代系列（除一个例外）对随机划分的CC
• Pharmaceutically active sulfanilide derivatives
  申请人：——

  公开号：US20040072816A1

  公开（公告）日：2004-04-15

  The present invention relates to sulfanilide derivatives of formula (I), in which R 1 and R 2 are optionally substituted aryl and heteroaryl groups and the other variables are as defined in the claims, for use as pharmaceutically active compounds, as well as pharmaceutical formulations containing such sulfanilide derivatives. Said derivatives are useful in the treatment and/or prevention of preterm labor, premature birth, dysmenorrhea, inappropriate secretion of vasopressin, congestive heart failure, arterial hypertension, liver cirrhosis, nephrotic syndrome and ocular hypertension. In particular, the present invention is related to sulfanilide derivatives displaying a substantial modulatory, in particular antagonistic activity, of the oxytocin and/or vasopressin receptor. More preferably, said compounds are useful in the treatment and/or prevention of disease states mediated by oxytocin and/or vasopressin, including preterm labor, premature birth, dysmenorrhea, inappropriate secretion of vasopressin, congestive heart failure, arterial hypertension, liver cirrhosis, nephrotic syndrome and ocular hypertension. The present invention is furthermore related to novel sulfanilide derivatives as well as to methods of their preparation.

  本发明涉及式(I)的磺胺基苯酰胺衍生物，其中R1和R2是可选择取代的芳基和杂环芳基基团，其他变量如权利要求中所定义，用作药用活性化合物，以及含有这种磺胺基苯酰胺衍生物的药物配方。所述衍生物在治疗和/或预防早产、早产、痛经、抗利尿素分泌不当、充血性心力衰竭、动脉高血压、肝硬化、肾病综合征和眼压增高方面具有用途。具体而言，本发明涉及显示对催产素和/或抗利尿素受体具有显著调节作用，特别是拮抗活性的磺胺基苯酰胺衍生物。更具体地说，所述化合物在治疗和/或预防由催产素和/或抗利尿素介导的疾病状态方面具有用途，包括早产、早产、痛经、抗利尿素分泌不当、充血性心力衰竭、动脉高血压、肝硬化、肾病综合征和眼压增高。本发明还涉及新型磺胺基苯酰胺衍生物以及其制备方法。
• Discovery and Development of a New Class of Potent, Selective, Orally Active Oxytocin Receptor Antagonists
  作者：Anna Quattropani、Jérôme Dorbais、David Covini、Pierre-André Pittet、Véronique Colovray、Russell J. Thomas、Richard Coxhead、Serge Halazy、Alexander Scheer、Marc Missotten、Guidon Ayala、Charles Bradshaw、Anne-Marie De Raemy-Schenk、Anthony Nichols、Rocco Cirillo、Enrico Gillio Tos、Claudio Giachetti、Lucia Golzio、Paolo Marinelli、Dennis J. Church、Claude Barberis、André Chollet、Matthias K. Schwarz

  DOI：10.1021/jm050645f

  日期：2005.12.1

  We report a novel chemical class of potent oxytocin receptor antagonists showing a high degree of selectivity against the closely related vasopressin receptors (V1a, V1b, V2). An initial compound, 7, was shown to be active in an animal model of preterm labor when administered by the intravenous but not by the oral route. Stepwise SAR investigations around the different structural elements revealed

  我们报告了一种新型的强力催产素受体拮抗剂的化学类别，它显示了对紧密相关的加压素受体（V1a，V1b，V2）的高度选择性。当通过静脉内而非口服途径给药时，最初的化合物7在早产的动物模型中显示出活性。围绕不同结构元件进行的逐步SAR研究表明，一个位置即芳烃磺酰基部分易于改变结构。因此，该位置用于引入各种取代基以改善物理化学性质。发现一些所得的类似物在体外效力和水溶性方面均优于7，这转化为在静脉内和口服施用后在动物模型中的功效显着改善。最好的化合物73
• Acid-Catalyzed Synthesis of Isatoic Anhydride-8-Secondary Amides Enables IASA Transformations for Medicinal Chemistry
  作者：Sudershan R. Gondi、Althaf Shaik、Kenneth D. Westover

  DOI：10.1021/acs.joc.1c02036

  日期：2022.1.7

  Quinazolin-dione-N-3-alklyl derivatives are the core scaffolds for several categories of bioactive small molecules, but current synthetic methods are costly, involve environmental hazards, and are not uniformly scalable. Here, we report an inexpensive, flexible, and scalable method for the one-pot synthesis of substituted quinazolin-dione-N-3-alkyls (isomers of isatoic-8-secondary amides (IASAs)) from

  喹唑啉二酮-N -3-烷基衍生物是几类生物活性小分子的核心支架，但目前的合成方法成本高，涉及环境危害，并且不能统一扩展。在这里，我们报告了一种廉价、灵活且可扩展的方法，用于从靛红中原位合成取代的喹唑啉-二酮-N -3-烷基（isatoic-8-仲酰胺 (IASAs) 的异构体）在酸性条件下捕获亚胺酸。我们进一步表明，该方法可用于合成多种具有药用用途的衍生物。