5-硝基吲哚-2-羧酸乙酯 | 16732-57-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 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: 5-硝基吲哚-2-羧酸乙酯
• 中文别名: 5-硝基吲哚-2-甲酸乙酯；5-硝基-1H-吲哚-2-羧酸乙酯；乙基5-硝基吲哚2-羧酸酯
• 英文名称: 5-nitro-indole-2-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-nitroindole-2-carboxylate；ethyl 5-nitro-1H-indole-2-carboxylate
• CAS: 16732-57-3
• 化学式: C₁₁H₁₀N₂O₄
• mdl: MFCD00216477
• 分子量: 234.211
• InChiKey: DVFJMQCNICEPAI-UHFFFAOYSA-N

物化性质

• 熔点：
  220-225 °C
• 沸点：
  376.52°C (rough estimate)
• 密度：
  1.3240 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 危险类别：
  IRRITANT
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储在阴凉干燥处。

SDS

Name:	Ethyl 5-Nitroindole-2-Carboxylate 95+% Material Safety Data Sheet
Synonym:
CAS:	16732-57-3

Section 1 - Chemical Product MSDS Name:Ethyl 5-Nitroindole-2-Carboxylate 95+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16732-57-3	Ethyl 5-Nitroindole-2-Carboxylate	95+	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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 immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Remove contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Get medical aid immediately. 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:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 16732-57-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Powder
Color: yellow-tan
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 223.00 - 225.00 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: negligible
Specific Gravity/Density:
Molecular Formula: C11H10N2O4
Molecular Weight: 234.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16732-57-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 5-Nitroindole-2-Carboxylate - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 16732-57-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16732-57-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16732-57-3 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

简介

5-硝基吲哚-2-甲酸乙酯是一种黄色至棕色的粉末状物质，可用作有机中间体。

用途

5-硝基吲哚-2-羧酸乙酯被用作合成吲哚-2-基乙酮的试剂。它还作为新型吲哚胺2,3-双加氧酶（IDO）抑制剂使用，并且是合成双杂芳基哌嗪（BHAP）逆转录酶抑制剂德拉维定的重要合成中间体。

制备

在250 mL 三颈瓶中加入80 mL 乙醇，40 mmol的5-硝基吲哚-2-羧酸以及1.0 mL 浓硫酸。室温下缓慢滴加浓硫酸，反应30小时（通过TLC跟踪）。反应结束后，浓缩至30 mL 后倒入60 mL 水中，并用20 mL 乙醚萃取两次。乙醚层用5%的碳酸钠溶液洗涤一次，再用水洗至中性，然后用无水硫酸镁干燥。最后蒸去乙醚得到黄色至棕色粉末状产物7.7 g 5-硝基吲哚-2-羧酸乙酯，收率为92.3%。

反应信息

• 作为反应物：
  描述：

  5-硝基吲哚-2-羧酸乙酯 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 37.0h， 生成 5-[[(1,1-二甲基乙氧基)羰基]氨基]-1H-吲哚-2-羧酸
  参考文献：
  名称：

  CC-1065类似物的葡糖苷酸衍生物的合成和初步细胞毒性研究。

  摘要：

  已经合成了带有CBI的CC-1065类似物的葡糖苷酸衍生物，并测试了其对U937白血病细胞的细胞毒性。新化合物在体外显示出有效的抗肿瘤活性。化合物1和2及其对应的葡糖醛酸苷3和4的IC（50）值分别为0.6、0.1、1.4和0.6 nM。葡糖苷酸3的毒性比其羟基对应物1低2倍，而葡糖醛酸4的毒性比其羟基对应物2低6倍。葡糖苷酸3和4在ADEPT方法中的用途可能有限。然而，它们可以常规方式用作抗肿瘤剂。

  DOI：

  10.1016/s0968-0896(02)00603-x
• 作为产物：
  描述：

  4-硝基苯肼 在 polyphosphoric acid 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 5-硝基吲哚-2-羧酸乙酯
  参考文献：
  名称：

  作为新型Nur77调节剂的5-（（（8-甲氧基-2-甲基喹啉-4-基）氨基）-1H-吲哚-2-碳酰肼衍生物的设计，合成和生物学评估。

  摘要：

  Nur77是治疗HCC等癌症的潜在靶标。在这里，我们详细介绍了新型的5-（（（8-甲氧基-2-甲基喹啉-4-基）氨基）-1 H-吲哚-2-碳酰肼衍生物作为潜在的Nur77调节剂系列。对目标化合物的抗增殖活性和Nur77结合亲和力的研究导致发现了领先的候选药物（10g），它是一种良好的Nur77结合剂（K D  = 3.58±0.16μM），对所有测试物质均具有广谱抗增殖活性肝癌细胞（IC 50  <2.0μM），对正常LO2细胞毒性低。10克可以上调Nur77的表达并介导Nur77的亚细胞定位以诱导肝癌细胞系的凋亡，这依赖于10g诱导Nur77依赖性自噬和内质网应激作为凋亡的上游。此外，体内试验证实10g显着抑制异种移植肿瘤的生长。这些结果表明10g有潜力被开发为靶向Nur77的新型抗肝癌药物。

  DOI：

  10.1016/j.ejmech.2020.112608

文献信息

• Design, synthesis and biological evaluation of methylenehydrazine-1-carboxamide derivatives with (5-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)-1H-indole scaffold: Novel potential CDK9 inhibitors
  作者：Hongyu Hu、Jun Wu、Mingtao Ao、Xiaoping Zhou、Boqun Li、Zhenzhen Cui、Tong Wu、Lijuan Wang、Yuhua Xue、Zhen Wu、Meijuan Fang

  DOI：10.1016/j.bioorg.2020.104064

  日期：2020.9

  previous work on the investigation of CDK9 inhibitors bearing indole moiety for the discovery of novel anticancer agents, novel methylenehydrazine-1-carboxamide derivatives with (5-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)-1H-indole scaffold were designed, synthesized, and evaluated for the CDK9 inhibitory activity and anticancer activity. Biological activity results demonstrated that most of these derivatives

  在我们以前的研究中，为了发现新型抗癌药，研究了带有吲哚部分的CDK9抑制剂，即具有（5-（（4-（吡啶-3-基）嘧啶-2-基）氨基）-1 H-吲哚支架的设计，合成及对CDK9抑制活性和抗癌活性的评估，生物学活性结果表明，这些衍生物大多数对CDK9的激酶活性具有良好的抑制作用，例如阻断其磷酸化功能和抑制其活性。抑制HIV-1转录化合物12i被发现是最有效的CDK9抑制剂，对HepG2，A375，MCF-7和A549表现出优异的抗癌活性，但对包括HaCaT和MCF-10A在内的正常细胞毒性较低。进一步的研究表明，由于CDK9抑制和随后抑制RNAPII CTD的丝氨酸2磷酸化的结果，代表性化合物12i剂量依赖性地增加了裂解的PARP水平，通过诱导癌细胞凋亡来发挥其抗增殖作用。最后，分子对接分析表明12i与CDK9具有良好的结合亲和力。总之，12i是有效的CDK9抑制剂，可以被认为是开发潜在抗癌药物的良好候选铅。
• Benzoxazepinones and their use as squalene synthase inhibitors
  申请人：——

  公开号：US20030078251A1

  公开（公告）日：2003-04-24

  There is disclosed a compound represented by the formula [I]: 1 wherein R 1 is optionally substituted 1-carboxyethyl group, optionally substituted alkyl-sulfonyl group, optionally substituted (carboxy-cycloalkyl)-alkyl group, —X 1 —X 2 —Ar—X 3 —X 4 —COOH (wherein X 1 and X 4 are a bond or alkylene group, X 2 and X 3 are a bond, —O—, —S—, Ar is divalent aromatic group etc.), R 2 is alkyl group optionally substituted with alkanoyloxy group and/or hydroxy group, R 3 is alkyl group, and W is halogen atom, etc., or a salt thereof. The compound has the cholesterol lowering activity and the triglyceride lowering activity and is useful for preventing and/or treating hyperlipidemia.

  披露了一种由公式[I]表示的化合物： 1 其中R 1 是可选地取代的1-羧乙基，可选地取代的烷基亚磺酰基，可选地取代的(羧基环烷基)-烷基，—X 1 —X 2 —Ar—X 3 —X 4 —COOH(其中X 1 和X 4 是键或亚烷基，X 2 和X 3 是键，—O—，—S—，Ar是二价芳香族等)，R 2 是可选地由酰氧基和/或羟基取代的烷基，R 3 是烷基，W是卤素原子等，或其盐。该化合物具有降低胆固醇活性和降低甘油三酯活性，用于预防或治疗高脂血症。
• Triamide-substituted heterobicyclic compounds
  申请人：Pfizer Inc.

  公开号：US20030187053A1

  公开（公告）日：2003-10-02

  The invention relates to triamide MTP/ApoB inhibitors of the formula 1 1 wherein R 1 -R 8 are as defined in the specification, as well as pharmaceutical compositions and uses thereof, and processes for preparing the compounds. The compounds of the invention are useful for the treatment of obesity and lipid disorders.

  本发明涉及三酰胺MTP/ApoB抑制剂，其化学公式为1，其中R1-R8如说明书所述，以及包含这些化合物的药物组合物及其用途，以及制备这些化合物的方法。本发明的化合物可用于治疗肥胖和脂质紊乱。
• Vanilloid receptor ligands and their use in treatments
  申请人：——

  公开号：US20030195201A1

  公开（公告）日：2003-10-16

  Compounds having the general structure 1 and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritis, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

  具有一般结构1的化合物以及含有它们的组合物，用于治疗急性疼痛、炎症性和神经性疼痛、牙痛、普通头痛、偏头痛、丛集性头痛、混合性血管和非血管综合症、紧张性头痛、一般炎症、关节炎、风湿病、骨关节炎、炎症性肠病、炎症性眼病、炎症性或不稳定的膀胱病、银屑病、具有炎症成分的皮肤疾病、慢性炎症状况、炎症性疼痛及其相关的过度疼痛和异常疼痛、神经性疼痛及其相关的过度疼痛和异常疼痛、糖尿病性神经病疼痛、灼痛、交感神经维持的疼痛、去神经综合症、哮喘、上皮组织损伤或功能障碍、单纯疱疹、在呼吸、生殖泌尿、胃肠或血管区域的内脏运动障碍、伤口、烧伤、过敏性皮肤反应、瘙痒、白癜风、一般胃肠病、胃溃疡、十二指肠溃疡、腹泻、由坏死性剂引起的胃部病变、毛发生长、血管运动性或过敏性鼻炎、支气管障碍或膀胱障碍。
• 一种制备吲哚膦酸酯衍生物的方法
  申请人：苏州大学张家港工业技术研究院

  公开号：CN104926868B

  公开（公告）日：2018-06-19

  本发明公开了一种制备吲哚膦酸酯衍生物的方法，具体为将吲哚衍生物、有机膦化合物、硝酸镁、4Å分子筛和催化量的碳酸银溶于溶剂中，于50～70℃下反应，获得吲哚膦酸酯衍生物；本发明使用吲哚衍生物为起始物，原料易得、种类很多；利用本发明的方法得到的产物类型多样，既可以直接使用、又可以用于其他进一步的反应；本发明采用碳酸银作为催化剂，无需有机配体，降低了成本，减少了污染；同时，反应条件温和、反应操作和后处理过程简单、产率高，适合于规模化生产。