4-(3-硝基-2-吡啶基)吗啉 | 24255-27-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 4-(3-硝基-2-吡啶基)吗啉
• 中文别名: N-(3-硝基-2-吡啶基)吗啉
• 英文名称: 4-(3-nitropyridin-2-yl)morpholine
• CAS: 24255-27-4
• 化学式: C₉H₁₁N₃O₃
• mdl: MFCD00452814
• 分子量: 209.205
• InChiKey: QMINJWUSSJFQBR-UHFFFAOYSA-N

物化性质

• 熔点：
  91-94°C
• 沸点：
  375.8±42.0 °C(Predicted)
• 密度：
  1.325

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  71.2
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Name:	4-(3-Nitro-2-pyridinyl)morpholine Material Safety Data Sheet
Synonym:
CAS:	24255-27-4

Section 1 - Chemical Product MSDS Name:4-(3-Nitro-2-pyridinyl)morpholine Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
24255-27-4	4-(3-Nitro-2-pyridinyl)morpholine	97+%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause respiratory tract irritation.
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:

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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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 24255-27-4: 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: Orange
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 89 - 90 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: C9H11N3O3
Molecular Weight: 209.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 24255-27-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(3-Nitro-2-pyridinyl)morpholine - 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
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 24255-27-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 24255-27-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 24255-27-4 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

反应信息

• 作为反应物：
  描述：

  4-(3-硝基-2-吡啶基)吗啉 在 bis-triphenylphosphine-palladium(II) chloride 盐酸 、 copper(l) iodide 、 硫酸 、 碘 、 铁粉 、 过碘酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-[5-(6-Amino-5-benzo[1,3]dioxol-5-ylpyrimidin-4-ylethynyl)-2-morpholin-4-ylpyridin-3-yl]-3-isopropylurea
  参考文献：
  名称：

  4-Amino-5-aryl-6-arylethynylpyrimidines: Structure–activity relationships of non-nucleoside adenosine kinase inhibitors

  摘要：

  A series of non-nucleoside adenosine kinase (AK) inhibitors is reported. These inhibitors originated from the modification of 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine (ABT-702). The identification of a linker that would approximate the spatial arrangement found between the pyrimidine ring and the aryl group at C(7) in ABT702 was a key element in this modification. A search of potential linkers led to the discovery of an acetylene moiety as a suitable scaffold. It was hypothesized that the aryl acetylenes, ABT-702, and adenosine bound to the active site of AK (closed form) in a similar manner with respect to the orientation of the heterocyclic base. Although potent acetylene analogs were discovered based on this assumption, an X-ray crystal structure of 5-(4-dimethylaminophenyl)-6-(6-morpholin-4-yipyridin-3-ylethynyl)pyrimidin-4-ylamine (16a) revealed a binding orientation contrary to adenosine. In addition, this compound bound tightly to a unique open conformation of AK. The structure-activity relationships and unique ligand orientation and protein conformation are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.029
• 作为产物：
  描述：

  吗啉 、 2-氯-3-硝基吡啶 在 二硫化碳 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以70%的产率得到4-(3-硝基-2-吡啶基)吗啉
  参考文献：
  名称：

  Three-component reaction between amines, carbon disulfide and electron-deficient derivatives of chloropyridine or chlorobenzene: synthesis of 3,6-diazaspiro[4.5]deca-2,7,9-trien-6-ium chloride and dithioylcarbamates derivatives

  摘要：

  在这项研究中，报道了在氯吡啶或氯苯的缺电子衍生物存在下，在CH3CN作为溶剂中，一些伯胺和仲胺与二硫化碳的三组分反应。伯胺与二硫化碳以及氯吡啶或氯苯的缺电子化合物反应 6-8 小时后得到三组分加成产物。仲胺与二硫化碳以及氯吡啶或氯苯的缺电子化合物反应 3-4 小时后得到双组分加成产物。反应产物通过重结晶或柱色谱纯化，并通过1H-NMR、13C-NMR、IR、UV和元素分析等光谱技术鉴定其结构。反应在温和条件下进行且不使用催化剂。

  DOI：

  10.1007/s13738-013-0300-y

文献信息

• NOVEL 2,6-SUBSTITUTED-3-NITROPYRIDINE DERIVATIVE, METHOD FOR PREPARING SAME, AND PHARMACEUTICAL COMPOSITION INCLUDING SAME
  申请人：Ryu Jei Man

  公开号：US20110306606A1

  公开（公告）日：2011-12-15

  The present invention relates to a novel 2,6-substituted-3-nitropyridine derivative compound, a method for preparing the same, and a pharmaceutical composition including the same for prevention and treatment of osteoporosis. The 2,6-substituted-3-nitropyridine derivative compound of the present invention increases osteoblast activity and effectively inhibits the differentiation of osteoclasts, and thus can be usefully used for the prevention and treatment of osteoporosis.

  本发明涉及一种新型的2,6-取代-3-硝基吡啶衍生物化合物，一种制备该化合物的方法，以及包括该化合物的用于预防和治疗骨质疏松症的药物组合物。本发明的2,6-取代-3-硝基吡啶衍生物化合物增加成骨细胞活性并有效抑制破骨细胞的分化，因此可用于预防和治疗骨质疏松症。
• NOVEL CARBAZOLE EHOP-016 DERIVATIVES AS ANTI-CANCER AND ANTI-MIGRATORY AGENTS
  申请人：UNIVERSITY OF PUERTO RICO

  公开号：US20190125746A1

  公开（公告）日：2019-05-02

  A series of novel of EHop-016 derivatives is presented herein via designing and synthesizing compounds that mimics its more favorable “U-shaped” conformation that appears to be critical for inhibitory activity against Rac. Based on modeling studies on EHop-016, compounds with a more rigid structural conformation can mimic this “U-shaped” conformation would improve the anti-migration activity against metastatic cells. Compounds are disclosed that inhibit RhoGTPases that are useful for inhibiting hyperprofilerative and neoplastic diseases. Specifically, the compounds inhibit the GTPases Rac and Cdc42 that are overactive or overexpressed in signaling pathways in cancer and metastasis. Methods for treatment of cancer and hyperproliferative diseases are disclosed.

  本文介绍了一系列EHop-016衍生物，通过设计和合成模拟其更有利的“U”形构象的化合物，这对于抑制Rac的活性至关重要。基于对EHop-016的建模研究，具有更严格结构构象的化合物可以模拟这种“U”形构象，从而提高对转移性细胞的抗迁移活性。披露了抑制对抗过度增殖和肿瘤性疾病有用的RhoGTP酶的化合物。具体来说，这些化合物抑制了在癌症和转移中信号通路中过度活跃或过度表达的Rac和Cdc42 GTP酶。还披露了治疗癌症和过度增殖性疾病的方法。
• HDAC抑制剂及其制备方法和用途
  申请人：成都先导药物开发股份有限公司

  公开号：CN111848591B

  公开（公告）日：2022-03-18

  本发明公开了一种式I所示的化合物、及其立体异构体、及其在药学上可接受的盐。本发明还涉及含有式I化合物的药物组合物以及该化合物在制备HDAC抑制剂类药物中的用途。本发明的化合物或其药物组合物可以用于治疗细胞增殖疾病、自身免疫疾病、炎症、神经变性疾病或病毒性疾病。
• Design, synthesis and biological evaluation of new carbazole derivatives as anti-cancer and anti-migratory agents
  作者：Cornelis P. Vlaar、Linette Castillo-Pichardo、Julia I. Medina、Cathyria M. Marrero-Serra、Ericka Vélez、Zulma Ramos、Eliud Hernández

  DOI：10.1016/j.bmc.2018.01.003

  日期：2018.2

  Based on the efficacy of EHop-016 as an inhibitor of migration and Rac1 activation, a new series of carbazole derivatives has been synthesized. Cytotoxic and anti-migratory effects of these compounds were evaluated in MCF-7 and MDA-MB-231 breast cancer cell lines. Preliminary investigations of their anticancer activity demonstrated that several compounds have moderate antiproliferative effects on cancer

  基于EHop-016作为迁移和Rac1激活抑制剂的功效，合成了一系列新的咔唑衍生物。在 MCF-7 和 MDA-MB-231 乳腺癌细胞系中评估了这些化合物的细胞毒性和抗迁移作用。对其抗癌活性的初步研究表明，几种化合物对 GI 50值在 13–50 µM 范围内的癌细胞系具有中等抗增殖作用。此外，化合物3b和11b分别抑制转移细胞系MDA-MB-231的迁移活性32%和34%。在 MDA-MB-231 和 MDA-MB-435 细胞系中，化合物11b在 250 nM 时可抑制 Rho GTPase Rac1 的激活 55%。与先导化合物 EHop-016 的 1.1 µM Rac1 抑制作用的IC 50相比，化合物11b 的体外功效提高了 4 倍。
• Nitrosation of Aryl and Heteroaryltrifluoroborates with Nitrosonium Tetrafluoroborate
  作者：Gary A. Molander、Livia N. Cavalcanti

  DOI：10.1021/jo300551m

  日期：2012.5.4

  converted into a variety of different substituents in a late synthetic stage. In this paper, we disclose a mild, selective, and convenient method for the ipso-nitrosation of organotrifluoroborates using nitrosonium tetrafluoroborate (NOBF4). Aryl- and heteroaryltrifluoroborates were converted into the corresponding nitroso products in good to excellent yields. This method proved to be tolerant of a broad range

  有机三氟硼酸盐已成为用于合成官能化芳基和杂芳基化合物的有毒和空气和水分敏感有机金属物种的替代品。已经表明，三氟硼酸盐部分可以很容易地在合成后期转化为各种不同的取代基。在本文中，我们公开了一种温和的，选择性的和方便的方法为本位使用亚硝鎓四氟硼酸盐（NOBF organotrifluoroborates的-nitrosation 4）。芳基和杂芳基三氟硼酸盐以良好到极好的收率转化为相应的亚硝基产物。这种方法被证明可以容忍广泛的官能团。