5-硝基芦竹碱 | 3414-64-0

• 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-硝基芦竹碱
• 英文名称: N,N-dimethyl-1-(5-nitro-1H-indol-3-yl)methanamine
• 英文别名: 5-nitrogramine；N,N-dimethyl-5-nitro-1H-indole-3-methanamine；Indole, 3-((dimethylamino)methyl)-5-nitro-
• CAS: 3414-64-0
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: SVNVKGIWGOHXPW-UHFFFAOYSA-N

物化性质

• 熔点：
  166-169°C
• 沸点：
  377.9±27.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Nitrogramine
Synonyms: Dimethyl[(5-nitro-1H-indol-3-yl)methyl]amine

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Nitrogramine
CAS number: 3414-64-0

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C11H13N3O2
Molecular weight: 219.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-硝基芦竹碱 在 sodium hydroxide 、 甲苯 作用下， 生成 5-硝基-DL-色氨酸
  参考文献：
  名称：

  Cavallini; Ravenna, Farmaco, Edizione Scientifica, 1958, vol. 13, p. 105,109

  摘要：

  DOI：
• 作为产物：
  描述：

  5-硝基吲哚 在 三氯氧磷 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 27.0h， 生成 5-硝基芦竹碱
  参考文献：
  名称：

  具有抗癌活性的新型 5-硝基吲哚衍生物作为 c-Myc G-四联体结合剂的合成和体外评价

  摘要：

  正在寻求针对c-Myc G-四联体 (G4) DNA 的化合物的先导化合物优化策略来开发抗癌药物。在这里，我们研究了基于吡咯烷取代的 5-硝基吲哚支架的新合成的一系列分子的结构-活性-关系 (SAR)，以靶向 G4 DNA。我们的合成系列允许使用结构保留的支架来调节柔性元件。生物学和生物物理分析表明，取代的 5-硝基吲哚支架与c-Myc启动子 G-四联体结合。这些化合物下调 c-Myc 表达并诱导癌细胞周期停滞在亚 G1/G1 期。它们进一步增加细胞内活性氧的浓度。 NMR 谱显示，三种新合成的化合物与末端 G 四联体（5'- 和 3'- 端）以 2:1 化学计量相互作用。

  DOI：

  10.1002/cmdc.202000835

文献信息

• Molecular iodine mediated oxidative cleavage of the C–N bond of aryl and heteroaryl (dimethylamino)methyl groups into aldehydes
  作者：Ketan S. Mandrekar、Santosh G. Tilve

  DOI：10.1039/d0nj05832g

  日期：——

  The oxidative cleavage of the C–N bond of aryl and heteroaryl (dimethylamino)methyl groups is achieved by employing molecular iodine as a mild oxidizing agent under ambient conditions in the presence of a mild base. The important reaction of C3 formylation of free NH and substituted indoles containing various substituents is accomplished from the corresponding Mannich bases. This methodology can also

  芳基和杂芳基（二甲基氨基）甲基的C–N键的氧化裂解可通过在环境条件下，弱碱存在下使用分子碘作为弱氧化剂来实现。游离NH和含有各种取代基的取代的吲哚的C 3甲酰化的重要反应是由相应的曼尼希碱完成的。该方法还可以扩展为芳基和其他杂芳基醛和酮的合成。此外，该方法的实用性已成功以克为单位进行了证明。
• Rhodium-Catalyzed Enantioselective Cyclization of 3-Allenyl-indoles: Access to Functionalized Tetrahydrocarbazoles
  作者：Christian P. Grugel、Bernhard Breit

  DOI：10.1021/acs.orglett.9b01721

  日期：2019.8.2

  A highly selective rhodium-catalyzed cyclization of tethered 3-allenylindoles is reported. In a smooth reaction, 1-vinyltetrahydrocarbazoles are obtained in excellent yields and enantioselectivities. Aside from a great functional group tolerance, this method requires neither the Schlenk technique nor the use of anhydrous solvents. Preliminary mechanistic investigations proved that the reaction proceeds

  报道了拴系的3-烯基吲哚的高选择性铑催化的环化。在平稳的反应中，以优异的产率和对映选择性获得了1-乙烯基四氢咔唑。除了对官能团的耐受性强之外，该方法既不需要Schlenk技术，也不需要使用无水溶剂。初步的机理研究证明，该反应通过中间形成的螺环吲哚胺进行，该螺环吲哚胺迅速经历酸催化的立体有规迁移。
• Ru-catalysed C–H silylation of unprotected gramines, tryptamines and their congeners
  作者：K. Devaraj、C. Sollert、C. Juds、P. J. Gates、L. T. Pilarski

  DOI：10.1039/c6cc00803h

  日期：——

  Selective Ru-catalysed C2-H silylation of heteroarenes is presented. The transformation works with or without directing group assistance and requires no protecting groups. Gramines and tryptamines may be converted efficiently whilst...

  提出了选择性Ru催化杂芳烃的C2-H甲硅烷基化。无论有没有直接的团体协助，这种转变都是有效的，并且不需要保护团体。谷氨酰胺和色胺可在...
• Rhodium-Catalyzed Diastereo- and Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines
  作者：Christian P. Grugel、Bernhard Breit

  DOI：10.1021/acs.orglett.9b03835

  日期：2019.12.6

  A highly selective rhodium-catalyzed tandem spirocyclization/reduction of 3-allenylindoles is reported. By employing a Hantzsch ester as reductant, vinylic spiroindolines are obtained in excellent yields as well as diastereo- and enantioselectivity. In addition, the reaction’s synthetic utility is highlighted by broad functional group compatibility and exemplified by a gram scale reaction with subsequent

  报道了3-烯基吲哚的高选择性铑催化的串联螺环化/还原。通过使用汉茨sch酯作为还原剂，可以获得优异的产率以及非对映和对映选择性的乙烯基螺二吲哚啉。另外，该反应的合成效用以广泛的官能团相容性突出，并以克级反应和随后的各种转化为例进行了举例说明。
• Indole derivatives thromboxane A2 antagonists
  申请人：Pfizer Inc.

  公开号：US05744488A1

  公开（公告）日：1998-04-28

  Compounds of formula (I): ##STR1## and pharmaceutically acceptable salt and biolabile esters thereof, wherein R.sup.1 is H, C.sub.1 -C.sub.4 alkyl, phenyl optionally substituted by up to three substituents independently selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen and CF.sub.3, or is 1-imidazolyl, 3-pyridyl or 4-pyridyl; R.sup.2 is H or C.sub.1 -C.sub.4 alkyl, R.sup.3 is SO.sub.2 R.sup.4 or COR.sup.4 where R.sup.4 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.3 perfluoroalkyl(CH.sub.2).sub.p, C.sub.3 -C.sub.6 cycloalkyl(CH.sub.2).sub.p, aryl(CH.sub.2).sub.p, or heteroaryl(CH.sub.2).sub.p, p being 0, 1 or 2, or R.sup.4 may be NR.sup.5 R.sup.6 where R.sup.5 is H or C.sub.1 -C.sub.4 alkyl and R.sup.6 is C.sub.1 -C.sub.6, alkyl, C.sub.3 -C.sub.6 cycloalkyl or aryl, or R.sup.5 and R.sup.6 together with the nitrogen atom to which they are attached form a 5- to 7-membered heterocyclic ring which may optionally incorporate a carbon-carbon double bond or a further heteroatom linkage selected from O, S, NH, N(C.sub.1 -C.sub.4 alkyl) and N(C.sub.1 -C.sub.5 alkanoyl); X is CH.sub.2 or a direct link, with the proviso that when R.sup.1 is 1-imidazolyl then X is CH.sub.2 ; m is 2, or 3; n is 0, 1 or 2, and wherein the group (CH.sub.2).sub.n NHR.sup.3 is attached at the 5-position when n is 0 or 1, or at the 5- or 4-position when n is 2. These compounds are selective TXA.sub.2 and PGH.sub.2 antagonists. Some also inhibit thromboxane synthetase.

  化合物的化学式为(I)：##STR1##及其药用可接受的盐和生物可降解酯，其中R.sup.1为H、C.sub.1 -C.sub.4烷基、苯基（可选择性地由高达三个从C.sub.1 -C.sub.4烷基、C.sub.1 -C.sub.4烷氧基、卤素和CF.sub.3中独立选择的取代基取代）、或者为1-咪唑基、3-吡啶基或4-吡啶基；R.sup.2为H或C.sub.1 -C.sub.4烷基，R.sup.3为SO.sub.2 R.sup.4或COR.sup.4，其中R.sup.4为C.sub.1 -C.sub.6烷基、C.sub.1 -C.sub.3全氟烷基(CH.sub.2).sub.p、C.sub.3 -C.sub.6环烷基(CH.sub.2).sub.p、芳基(CH.sub.2).sub.p或杂环芳基(CH.sub.2).sub.p，p为0、1或2，或者R.sup.4可以为NR.sup.5R.sup.6，其中R.sup.5为H或C.sub.1 -C.sub.4烷基，R.sup.6为C.sub.1 -C.sub.6烷基、C.sub.3 -C.sub.6环烷基或芳基，或者R.sup.5和R.sup.6与它们连接的氮原子一起形成一个5-到7-成员杂环，该环可以选择性地包含一个碳-碳双键或进一步的杂原子连接，选自O、S、NH、N(C.sub.1 -C.sub.4烷基)和N(C.sub.1 -C.sub.5醇酰基)；X为CH.sub.2或直接连接，但当R.sup.1为1-咪唑基时，X为CH.sub.2；m为2或3；n为0、1或2，其中(CH.sub.2).sub.nNHR.sup.3基团在n为0或1时连接在5位，或在n为2时连接在5位或4位。这些化合物是选择性的TXA.sub.2和PGH.sub.2拮抗剂。有些还抑制TXA合成酶。