6-溴芦竹碱 | 59609-63-1

• 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: 6-溴芦竹碱
• 英文名称: 6-Bromogramine
• 英文别名: 6-Bromgramin；1-(6-Bromo-1H-indol-3-yl)-N,N-dimethylmethanamine
• CAS: 59609-63-1
• 化学式: C₁₁H₁₃BrN₂
• 分子量: 253.142
• InChiKey: CKUNQRCQLWHINE-UHFFFAOYSA-N

物化性质

• 熔点：
  136-139 °C(Solv: ligroine (8032-32-4))
• 沸点：
  346.9±27.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 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：
  19
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 6-Bromogramine
Synonyms: [(6-Bromo-1H-indol-3-yl)methyl]dimethylamine

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 6-Bromogramine
CAS number: 59609-63-1

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C11H13BrN2
Molecular weight: 253.1

---

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, hydrogen bromide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6-溴芦竹碱 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 6-溴吲哚-3-乙酸
  参考文献：
  名称：

  Total Synthesis of (±)-Chartelline C

  摘要：

  The first total synthesis of (+/-)-chartelline C in a concise 10-step sequence is reported. Highlights of the completion of this decades-old puzzle include (1) chemo- and position-selective installation of the heteroaromatic halogens, (2) halogen-sparing monoreduction of an alkyne linker, (3) a simple strategy for placement of the sensitive beta-chloroenamide, (4) an unusually facile thermolysis of a vinyl carboxylic acid, and (5) a powerful ring contraction whose potential utility in heterocyclic chemistry merits further investigation.

  DOI：

  10.1021/ja0659673
• 作为产物：
  描述：

  芦竹碱 生成 6-溴芦竹碱
  参考文献：
  名称：

  SETTIMO, A. DA;PRIMOFIORE, G.;FERRARINI, P. L.;FRANZONE, J. S.;CIRILLO, R+, EUR. J. MED. CHEM., 1983, 18, N 3, 261-267

  摘要：

  DOI：

文献信息

• Synthesis of tryptophans by alkylation of chiral glycine enolate equivalents with quaternary gramines
  作者：Matiss Reinfelds、Konstantins Kalinins、Dace Katkevica、Ronalds Zemribo、Martins Katkevics

  DOI：10.1016/j.tetlet.2015.09.017

  日期：2015.10

  source of the 3-methylindole fragment for diastereoselective alkylation. The best yields and stereoselectivity were obtained for the alkylation of a chiral William’s morpholinone enolate. Based on this transformation, a general method for the synthesis of enantiopure, indole ring substituted tryptophan derivatives was developed with good overall yields.

  发现季胺是非对映选择性烷基化的3-甲基吲哚片段的合适来源。对于手性William's吗啉代烯醇烯酸酯的烷基化，可获得最佳收率和立体选择性。基于该转化，开发了具有良好总收率的对映体纯的，吲哚环取代的色氨酸衍生物的合成的通用方法。
• Methods and compounds for treating proliferative diseases
  申请人：——

  公开号：US20040048915A1

  公开（公告）日：2004-03-11

  The compounds disclosed herein are indolocarbazoles of Formula (I), which are potent CDK4 inhibitors, and are useful in the treatment of cell proliferative disorders, including cancer. Formula (I). 1

  本公开的化合物是式(I)的吲哚咔巴醌，它们是有效的CDK4抑制剂，并且在治疗细胞增殖性疾病，包括癌症方面具有用处。Formula (I).
• Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides
  作者：Vaishnavi N. Nair、Volga Kojasoy、Croix J. Laconsay、Wang Yeuk Kong、Dean J. Tantillo、Uttam K. Tambar

  DOI：10.1021/jacs.1c00283

  日期：2021.6.23

  metal-coordinated ion-pair in the copper catalyzed [1,2]-rearrangement that recombines in the solvent-cage. The application of our methodology was demonstrated in the first total synthesis of the indole alkaloid (±)-sorazolon B, which enabled the stereochemical reassignment of the natural product. Further functional group transformations of the rearrangement products to generate valuable synthetic intermediates

  我们开发了由吲哚底物衍生的鎓叶立德的催化剂控制区域发散重排。由取代的吲哚原位形成的氧鎓叶立德分别在铑和铜催化剂存在下选择性地进行[2,3]-和[1,2]-重排。实验和密度泛函理论 (DFT) 相结合的计算研究表明，不同的机制途径涉及铑催化反应中的无金属叶立德有利于 [2,3]-重排，以及铜催化反应中的金属配位离子对 [1 ,2]-在溶剂笼中重新组合的重排。我们的方法的应用在吲哚生物碱 (±)-sorazolon B 的首次全合成中得到了证明，这使得天然产物的立体化学重新分配成为可能。还展示了重排产物的进一步官能团转化以产生有价值的合成中间体。
• New synthetic approach to paullones and characterization of their SIRT1 inhibitory activity
  作者：Sara Soto、Esther Vaz、Carmela Dell'Aversana、Rosana Álvarez、Lucia Altucci、Ángel R. de Lera

  DOI：10.1039/c2ob06695e

  日期：——

  A series of 7,12-dihydroindolo[3,2-d][1]benzazepine-6(5H)-ones (paullones) substituted at C9/C10 (Br) and C2 (Me, CF3, CO2Me) have been synthesized by a one-pot Suzuki–Miyaura cross-coupling of an o-aminoarylboronic acid and methyl 2-iodoindoleacetate followed by intramolecular amide formation. Other approaches to the paullone scaffold based on Pd-catalyzed C–H activation were unsuccessful. In vitro enzymatic assay with recombinant human SIRT-1 indicated a strong inhibitory profile for the series, in particular the analogue with a methoxycarbonyl group at C2 and a bromine at C9. These compounds are, in general, inducers of granulocyte differentiation of the U937 acute leukemia cell line and cause a marked increase in pre-G1 of the cell cycle.

  一系列9,10-二溴代和2-甲基、2-三氟甲基、2-甲氧羰基取代的7,12-二氢吲哚并[3,2-d][1]苯并氮杂环庚-6(5H)-酮（paullones）通过一锅法Suzuki-宫浦交叉偶联反应合成，该方法涉及邻氨基芳基硼酸和甲基2-碘吲哚乙酸酯的反应，随后进行分子内酰胺化。基于钯催化的C-H活化的其他制备paullone骨架的方法未获成功。体外酶学分析显示，这些化合物对重组人SIRT-1具有强烈的抑制作用，尤其是2-甲氧羰基和9-溴代的类似物。这些化合物一般都能诱导U937急性白血病细胞系的粒细胞分化，并显著增加细胞周期中的前G1期。
• Synthesis and Preclinical Evaluation of 6-[¹⁸F]Fluorine-α-methyl-<scp>l</scp>-tryptophan, a Novel PET Tracer for Measuring Tryptophan Uptake
  作者：Raisa Krasikova、Mikhail Kondrashov、Camilla Avagliano、Mikhail Petukhov、Ana Vazquez-Romero、Evgeny Revunov、Peter Johnström、Lenke Tari、Miklós Tóth、Jenny Häggkvist、Sophie Erhardt、Simon Cervenka、Magnus Schou

  DOI：10.1021/acschemneuro.0c00135

  日期：2020.6.17

  The positron emission tomography (PET) radioligand α-[11C]methyl-l-tryptophan ([11C]AMT) has been used to assess tryptophan metabolism in cancer, epilepsy, migraine, and autism. Despite its extensive application, the utility of this tracer is currently hampered by the short half-life of the radionuclide used for its labeling (11C, t1/2 = 20.4 min). We herein report the design, synthesis, radiolabeling

  正电子发射断层扫描（PET）放射配体α-[ 11 C]甲基-1-色氨酸（[ 11 C] AMT）已用于评估癌症，癫痫，偏头痛和自闭症中的色氨酸代谢。尽管其广泛应用，但示踪剂的实用性目前仍因其标记所用放射性核素的半衰期短（11 C，t 1/2 = 20.4分钟）而受到阻碍。我们在此报告了在芳香环的6位上氟化的氟18（18 F，t 1/2 = 109.7分钟）标记的类似物的设计，合成，放射性标记和体内初步评估（[ 18F] 6-F-AMTr）。在使用PET的小鼠中[ 18 F] 6-F-AMTr和[ 11 C] AMT进行的头对头比较中，两种示踪剂的峰值脑放射性，区域性脑分布和动力学特征相似。但是[ 18 F] 6-F-AMTr不是体外酶法测定的IDO1或TPH的底物。因此，示踪剂的大脑摄取更可能与LAT1在血脑屏障上的转运有关，而不是沿血清素或犬尿氨酸途径的代谢。