9-肼基吖啶 | 3407-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 9-肼基吖啶
• 中文别名: 吖啶-9-基肼；对-肼基吖啶；9-吖啶基肼；吖啶,9-肼基-
• 英文名称: 9-hydrazinoacridine
• 英文别名: (acridin-9-yl)hydrazine；9-Hydrazino-acridin；acridin-9-ylhydrazine
• CAS: 3407-93-0
• 化学式: C₁₃H₁₁N₃
• mdl: MFCD00051330
• 分子量: 209.25
• InChiKey: SVANEUDZNISLJD-UHFFFAOYSA-N

物化性质

• 熔点：
  177 °C
• 沸点：
  338.61°C (rough estimate)
• 密度：
  1.1847 (rough estimate)
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与不相容材料及水分直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  T+,Xi
• 安全说明：
  S1,S28A,S36/37/39,S45
• 危险类别码：
  R28
• 海关编码：
  2933990090
• 储存条件：
  密封储存于阴凉干燥处，冷藏温度应保持在-20℃。

SDS

Name:	9-Hydrazinoacridine hydrochloride 98% Material Safety Data Sheet
Synonym:
CAS:	3407-93-0

Section 1 - Chemical Product MSDS Name:9-Hydrazinoacridine hydrochloride 98% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3407-93-0	9-Hydrazinoacridine hydrochloride	98%	unlisted

Hazard Symbols: T+
Risk Phrases: 23/24 28

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation and in contact with skin. Very toxic if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Toxic in contact with skin.
Ingestion:
May be fatal if swallowed. May cause irritation of the digestive tract.
Inhalation:
May cause respiratory tract irritation. Toxic if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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 immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid immediately. Wash mouth out with water.
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.
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 agent most appropriate to extinguish fire.

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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:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Deep freeze (below -20C). Poison room locked.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 3407-93-0: 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: Crystalline powder
Color: ochre
Odor: acetic odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 301-305 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: C13H11N3.HCl
Molecular Weight: 245.71

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, moisture.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3407-93-0: AR9321500 LD50/LC50:
Not available.
Carcinogenicity:
9-Hydrazinoacridine hydrochloride - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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: I
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: I
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: T+
Risk Phrases:
R 23/24 Toxic by inhalation and in contact with
skin.
R 28 Very toxic if swallowed.
Safety Phrases:
S 1 Keep locked up.
S 28A After contact with skin, wash immediately with
plenty of water.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 38 In case of insufficient ventilation, wear
suitable respiratory equipment.
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# 3407-93-0: No information available.
Canada
CAS# 3407-93-0 is listed on Canada's NDSL List.
CAS# 3407-93-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3407-93-0 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法

用9-氯代吖啶在铂及少量碱存在下与肼加热制得。

合成制备方法

同样使用9-氯代吖啶，在铂和少量碱的存在下与肼加热制得。

用途简介

用作有机合成中间体。

用途

用作有机合成中间体。

反应信息

• 作为反应物：
  描述：

  9-肼基吖啶 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 26.5h， 生成 2'-(9,10-dihydroacridin-9-ylidene)hydrazono-3'-methyl-4'-imino-1',3'-thiazolidine
  参考文献：
  名称：

  丙烯腈硫代氨基脲在1,3-噻唑烷合成中的立体化学，互变异构和反应†

  摘要：

  用各种异硫氰酸酯（RNCS，R ＝甲基，烯丙基，苯基，对-甲氧基苯基和对-硝基苯基）处理后的Acridin-9-基肼产生了相应的硫代氨基脲，在a环类型的一面上取代了cr啶。烷基取代的化合物以主要的H-10，H-12互变异构体（E或Z或两者均与C 13 -N 14键有关）和次要的H-10，SH互变异构体（其中一个为平衡）形式存在于溶液中。E或Z或两者）。芳族取代化合物的主要种类是H-10，H-12 E互变异构体，明显的次要种类是H-10，H-12 Z互变异构体。在用亚甲基腈氧化物处理后，将每一种硫代氨基脲均定量地转化成类似的氨基脲，其中所有结构均以具有关于C 13 -N 14键的Z构象的H-10互变异构体的形式存在于溶液中。所述化合物与碘甲烷的甲基化产生S-甲基化的化合物，其中Z构型在每种情况下均沿N 12 -C 13双键在E构型上占优势。用溴乙酸甲酯处理硫代氨基脲会形成1'，3'-噻唑烷定

  DOI：

  10.1002/jhet.5570430318
• 作为产物：
  描述：

  9-氯吖啶 在 肼 作用下， 生成 9-肼基吖啶
  参考文献：
  名称：

  带有新隐油菜籽，a啶和α-氨基膦酸酯支架的新杂种的合成及其抗增殖活性

  摘要：

  新型α-氨基膦酸酯杂化物8a-f的合成是在高氯酸锂作为路易斯酸催化剂在甲醇中的条件下，使11-苯氧基-4-甲酰基新隐油菜籽油3，氨基烷基氨基a啶6a-f和亚磷酸二苯酯7反应完成的。在碳酸钾存在下，DMF中11-氯代新隐油菜碱1与4-羟基苯甲醛2反应得到起始醛3，而9-氯代ac啶4与适当的二胺5a-f反应合成9-氨基烷基氨基a啶6a -f。。所有合成的杂种的结构通过光谱学方法确认，并显示与预期结构一致的光谱。评估了所有合成杂种对HCT-116，MCF-7，HepG2和A549人癌细胞系的抗增殖活性。筛选结果证明，大多数报道的化合物都是有效的，尤其是杂种8a，其对MCF-7，HepG2和A549癌细胞的活性最高，分别为IC 50 8.2、23.1和19.4 µM。该活性明显高于标准药物阿霉素。此外，杂种8f对HCT-116癌细胞系表现出最有效的活性，IC 50比参考药物阿霉素（IC 50）高2

  DOI：

  10.1007/s13738-019-01849-2

文献信息

• Design, synthesis and evaluation of acridin-9-yl hydrazide derivatives as BACE-1 inhibitors
  作者：Priti Jain、Pankaj K. Wadhwa、Hemant R. Jadhav

  DOI：10.1007/s00044-016-1581-3

  日期：2016.7

  hydrazide derivatives, known to inhibit other aspartyl proteases. The derivatives were designed based on the docking study, synthesized and assessed for BACE-1 inhibition in vitro. Docking simulation predicted the binding of prototype acridin-9-yl hydrazide at BACE-1 active site. The enzyme–inhibitor complex was primarily stabilized by hydrogen bonds between the hydrazide part of the inhibitor and side

  BACE-1，一种天冬氨酰蛋白酶，与阿尔茨海默氏病有关。在本文中，我们报告了已知可抑制其他天冬氨酰蛋白酶的acridin-9-酰肼衍生物的BACE-1抑制潜力。基于对接研究设计衍生物，合成并评估其对BACE-1的体外抑制作用。对接模拟预测原型Acridin-9-酰肼在BACE-1活性位点的结合。酶-抑制剂复合物主要通过抑制剂的酰肼部分与Gly11的侧链之间的氢键稳定，Gly11是10s环的重要氨基酸。cri啶基部分与Tyr71呈π-π堆积，而苯环则埋在S1腔中。酶抑制实验表明，所合成的化合物对化合物AA-13具有中等活性 在10 µM浓度下具有54.54％的抑制作用。
• Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides
  作者：Jana Tomaščiková、Ján Imrich、Ivan Danihel、Stanislav Böhm、Pavol Kristian、Jana Pisarčíková、Marián Sabol、Karel Klika

  DOI：10.3390/molecules13030501

  日期：——

  A series of 1-acyl-4-phenyl/(acridin-9-yl)thiosemicarbazides 3, including fournew compounds, were prepared in order to study substituent effects on cyclizationreactions with oxalyl chloride (producing imidazolidine-4,5-diones 4), dimethylacetylenedicarboxylate (to give thiazolidin-4-ones 7 and 8) and autocondensation underalkaline conditions (to yield 1,2,4-triazoles 9). A positional isomer, 10 of compound 3f wasalso prepared. Altogether, twenty new compounds characterized and identified by IR, UV,1H, 13C and 2D NMR and quantum chemical calculations are described. The tautomerismof the products and regioselectivity of the reactions were evaluated. Compounds 3f−h,3h·2HCl, 7b,d and 10 were screened for cytotoxic activity against the L1210 leukemia cellline and all compounds, except for 3f, exhibited promising inhibitions of cell growth.

  制备了一系列 1-酰基-4-苯基/(吖啶-9-基)硫代氨基脲 3，包括四种新化合物，以研究取代基对与草酰氯（生成咪唑烷-4,5-二酮 4）、二甲基乙酰二甲酸酯（生成噻唑烷-4-酮 7 和 8）和碱性条件下自缩合（生成 1,2,4-三唑 9）的环化反应的影响。此外，还制备出了化合物 3f 的位置异构体 10。通过红外光谱、紫外光谱、1H、13C 和 2D NMR 以及量子化学计算，共描述和鉴定了 20 种新化合物。对产物的同分异构和反应的区域选择性进行了评估。化合物 3f-h、3h-2HCl、7b、d 和 10 对 L1210 白血病细胞进行了细胞毒活性筛选，除 3f 外，所有化合物都表现出良好的细胞生长抑制作用。
• Heterocyclization of (Acridin-9-yl)thiosemicarbazides with Dimethyl Acetylenedicarboxylate
  作者：Jana Tomaščiková、Ján Imrich、Ivan Danihel、Stanislav Böhm、Pavol Kristian

  DOI：10.1135/cccc20070347

  日期：——

  Two types of (acridin-9-yl)thiosemicarbazides with the acridine moiety in the thiourea part (Acr-NHCS, 10a, 10b) and hydrazine part (Acr-NHNHCS, 12a-12c) were prepared to investigate their reactions with dimethyl acetylenedicarboxylate. Five-membered thiazolidinone derivatives 15a, 15b, 19a-19c were formed; some aspects of corresponding reaction mechanisms are discussed. 1D and 2D ¹H and ¹³C NMR spectroscopy and DFT quantum chemical calculations were used to elucidate the structure of the compounds.

  两种(acridin-9-yl)硫脲类化合物，一种是在硫脲部分含有九氮杂蒽基团的(Acr-NHCS,10a,10b)，另一种是在肼部分含有九氮杂蒽基团的(Acr-NHNHCS,12a-12c)，用于研究它们与二甲基乙炔二羧酸的反应。形成了五元杂环噻唑啉酮衍生物15a、15b、19a-19c；讨论了相应反应机理的某些方面。使用1D和2D ¹H和¹³C NMR光谱和DFT量子化学计算来阐明化合物的结构。
• [EN] NOVEL HDMX INHIBITORS AND THEIR USE FOR CANCER TREATMENT<br/>[FR] NOUVEAUX INHIBITEURS HDMX ET LEUR UTILISATION DANS LE TRAITEMENT DU CANCER
  申请人：MIRX PHARMACEUTICALS LLC

  公开号：WO2015153535A1

  公开（公告）日：2015-10-08

  The present invention provides for novel acridine-like class of compounds that have demonstrated efficiency in treating cancer. The compounds of the present invention have demonstrated efficacy in binding to and antagonizing the activity of the p53 repressor, HDMX. Once administered to a cell, the compounds of the present invention bind HDMX, thereby allowing p53 to induce apoptosis of the cancerous cell. A combination of this class of compounds along with Nutlin3 provides a novel approach to treat cancers.

  本发明提供了一种新型的类似于吖啶的化合物，已经证明可以有效地治疗癌症。本发明的化合物已经证明在结合并拮抗p53抑制剂HDMX的活性方面具有疗效。一旦这些化合物被注入细胞，它们会与HDMX结合，从而使p53诱导癌细胞凋亡。将这类化合物与Nutlin3结合使用可以提供一种治疗癌症的新方法。
• Synthesis of substituted acridinyl pyrazoline derivatives and their evaluation for anti-inflammatory activity
  作者：Trilok Chandra、Neha Garg、Suman Lata、K.K. Saxena、Ashok Kumar

  DOI：10.1016/j.ejmech.2010.01.009

  日期：2010.5

  A rapid preparation of compounds (1–24), with the objective of discovering novel and potent anti-inflammatory agent. All the compounds exhibited anti-inflammatory and analgesic activities at the dose 50 mg/kg p.o. The compound 1-(2′,4′-Chloroacridine-9′-yl)-3-(5′-pyridine-4-yl)-(1,3,4-oxadiazol-2-yl-thiomethyl)-pyrazole-5-one 24 showed better anti-inflammatory and analgesic activities at the three

  一种快速制备化合物（的1 - 24），与所述目标发现新颖的和有效的抗炎剂。所有化合物在剂量为50 mg / kg时均具有抗炎和镇痛作用。化合物1-（2'，4'-氯cr啶-9'-基）-3-（5'-吡啶-4-基）- （1,3,4-恶二唑-2-基-硫甲基）-吡唑-5-酮24在25、50和100 mg / kg po的三个分级剂量下显示出更好的抗炎和镇痛活性