1-(3-chloropropyl)-4-methylpiperazine dihydrochloride | 2031-23-4

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(3-chloropropyl)-4-methylpiperazine dihydrochloride
• 英文别名: 3-(4-methyl-1-piperazinyl)propyl chloride dihydrochloride；1-(3-Chloropropyl)-4-methylpiperazine hydrochloride；1-(3-chloropropyl)-4-methylpiperazine;hydrochloride
• CAS: 2031-23-4
• 化学式: C₈H₁₇ClN₂*2ClH
• 分子量: 249.611
• InChiKey: OOGLQRQSPQVQTE-UHFFFAOYSA-N

物化性质

• 熔点：
  255-257 °C (decomp)(Solv: ethanol (64-17-5))
• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  6.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933599090
• WGK Germany：
  3

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 1-(3-Chloropropyl)-4-methylpiperazine DiHCl
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 1-(3-Chloropropyl)-4-methylpiperazine DiHCl
CAS number: 2031-23-4

---

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: C8H17ClN2.2ClH
Molecular weight: 249.6

---

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 chloride.

---

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

制备方法与用途

该化合物1-(3-氯丙基)-4-甲基哌嗪二盐酸盐可用于医药化工中的合成中间体。

反应信息

• 作为反应物：
  描述：

  1-(3-chloropropyl)-4-methylpiperazine dihydrochloride 在 sodium azide 、 potassium carbonate 作用下， 以 水 为溶剂， 生成 1-(3-azidopropyl)-4-methylpiperazine
  参考文献：
  名称：

  “点击化学”合成具有1,2,3-三唑部分的新型天然产物笼养型氧杂蒽，其具有改善的类药物性质，作为口服活性抗肿瘤剂。

  摘要：

  DDO-6101是一种类似天然产物的笼状x吨酮，以前是在我们的实验室中基于藤黄天然产物藤黄酸（GA）的药效团构架发现的，在体外显示出强的细胞毒性，但由于其不良的类药物特性而在体内的疗效较差。为了改善类药物性质和体内抗肿瘤能力，已经通过“点击化学”有效地合成了一系列新的十种带有三唑的笼状黄酮酮DDO-6101衍生物，并评估了它们的体外抗肿瘤活性和类药物性质。大多数目标化合物对A549，HepG2，HCT116和U2OS癌细胞具有持续的细胞毒性，并具有改善的水溶性和通透性。值得注意的是，这些笼罩的氧杂蒽酮还对紫杉醇抗性或顺铂抗性的A549癌细胞具有活性。考虑到体外活性和类药物性质，化合物8g已被推进体内功效实验。结果显示，在A549移植的小鼠模型中，静脉内或经口给药8g（命名为DDO-6318）比先导DDO-6101更有效，并且它可能是有希望的抗肿瘤候选药物，可以进一步评估。

  DOI：

  10.3390/molecules22111834
• 作为产物：
  描述：

  1-(3-氯丙基)-4-甲基哌嗪 在 盐酸 作用下， 以 乙醚 为溶剂， 以100%的产率得到1-(3-chloropropyl)-4-methylpiperazine dihydrochloride
  参考文献：
  名称：

  硫脲和氨基硫脲衍生物：结构、转化和药理活性。三嗪基和咪唑并吲哚的保肝作用

  摘要：

  用于治疗肝脏疾病的众所周知的保肝药的功效不足[1]。考虑到外伤性、毒性和感染引起的肝损伤的永久性增长 [2]，目前寻找具有保肝活性的新药很有意义。我们决定在 1,2,4-triazinoindole 衍生物系列中进行这项研究，其分子含有硫脲片段 [3 5]。由于已知抗氧化剂的保肝活性是典型的[6]，这些化合物值得研究，因为它们具有抑制脂质过氧化过程和稳定膜功能的能力[5]。此外，该系列的一些化合物能够抑制肝脏的微粒体氧化系统 [7]。在这方面，通过与微粒体氧化抑制剂 dithioearb 和相关制剂的类比，我们有理由预期这些化合物中存在保肝活性，这可能与保肝毒物的有毒代谢物的产生减少有关 [8]。此外，我们考虑到加速肝脏再生的一种可能方法是利用三嗪基吲哚衍生物作用于相关免疫机制的能力[9]。在本研究中，我们合成了一系列 1,2,4-三嗪基 [5,6-b] 吲哚衍生物 (Ia I s ) 和异构的

  DOI：

  10.1007/bf02645993

文献信息

• 2,4-diamino pyrimidine compounds having anti-cell proliferative activity
  申请人：AstraZeneca AB

  公开号：US06593326B1

  公开（公告）日：2003-07-15

  A pyrimidine derivative of formula (I): wherein: R1 is an optional substituent as defined within; Rx is selected from halo, hydroxy, nitro, amino, cyano, mercapto, carboxy, sulphamoyl, formamido, ureido or carbamoyl or a group of formula (Ib): A—B—C— as defined within; Q1 and Q2 are independently selected from aryl, a 5- or 6-membered monocyclic moiety; and a 9- or 10-membered bicyclic heterocyclic moiety; and one or both of Q1 and Q2 bears on any available carbon atom one substituent of formula (Ia) as defined within; and Q1 and Q2 are optionally further substituted; or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof; are useful as anti-cancer agents; and processes for their manufacture and pharmaceutical compositions containing them are described.

  式（I）的嘧啶衍生物： 其中：R1是如定义的可选取代基；Rx选自卤素、羟基、硝基、氨基、氰基、巯基、羧基、磺胺基、甲酰胺基、脲基或氨基甲酰基或如定义的式（Ib）的基团：A—B—C—；Q1和Q2独立选自芳基、5-或6-成员单环基；和9-或10-成员双环杂环基；Q1和Q2中的一个或两个在任一可用碳原子上带有如定义的式（Ia）的取代基；Q1和Q2可进一步取代；或其药学上可接受的盐或体内水解酯；可用作抗癌剂；并描述了其制备方法和含有它们的药物组合物。
• Design, synthesis and evaluation of 6-aryl-indenoisoquinolone derivatives dual targeting ERα and VEGFR-2 as anti-breast cancer agents
  作者：Zhichao Tang、Chengzhe Wu、Tianlin Wang、Kejing Lao、Yejun Wang、Linyi Liu、Moses Muyaba、Pei Xu、Conghui He、Guoshun Luo、Zhouyang Qian、Shaoxiong Niu、Lijun Wang、Ying Wang、Hong Xiao、Qidong You、Hua Xiang

  DOI：10.1016/j.ejmech.2016.04.029

  日期：2016.8

  The estrogen receptors have played important roles in breast cancer development and progression. Selective estrogen receptor modulators, such as Tamoxifen, have showed great benefits in the treatment and prevention of breast cancer. But the disadvantages of induction of endometrial cancer and drug resistance have limited their use. Multiple ligand which act at multiple biomolecular targets may exert

  雌激素受体在乳腺癌的发生和发展中起着重要的作用。选择性雌激素受体调节剂，如他莫昔芬，在乳腺癌的治疗和预防中显示出巨大的益处。但是诱导子宫内膜癌和耐药性的缺点限制了它们的使用。作用于多个生物分子靶标的多个配体可以发挥有益的优点，即具有提高的功效和较低的副作用发生率。在这项工作中，我们描述了一系列的6-芳基-茚基异喹诺酮衍生物作为ERα和VEGFR-2双重抑制剂的合成和评估。这些化合物具有良好的ERα结合亲和力和ERα拮抗活性，以及​​强大的VEGFR-2抑制能力。他们还具有出色的抗MCF-7，MDA-MB-231，石川和HUVEC细胞系。选择性化合物的进一步研究21c显示它能够抑制MCF-7细胞中VEGFR-2的激活和Raf-1 / MAPK / ERK途径的信号转导。
• Manganese-Catalyzed Anti-Markovnikov Hydroamination of Allyl Alcohols via Hydrogen-Borrowing Catalysis
  作者：Kuhali Das、Koushik Sarkar、Biplab Maji

  DOI：10.1021/acscatal.1c01199

  日期：2021.6.18

  In this article, a selective formal anti-Markovnikov hydroamination of allyl alcohols is presented. It enables the versatile synthesis of valuable γ-amino alcohol building blocks. A phosphine-free Earth’s abundant manganese(I) complex catalyzed the reaction under hydrogen-borrowing conditions. A vast range of aliphatic, aromatic amines, drug molecules, and natural product derivatives underwent successful

  控制加氢胺化反应的选择性对于胺的多样化来说是一项极具挑战性但非常理想的任务。在本文中，介绍了烯丙醇的选择性正式反马尔科夫尼科夫加氢胺化。它使有价值的 γ-氨基醇构建块的多功能合成成为可能。一种不含磷的地球上丰富的锰 (I) 配合物在借氢条件下催化了该反应。大量的脂肪族、芳香族胺、药物分子和天然产物衍生物与具有优异官能团耐受性的伯烯和仲烯丙醇成功加氢胺化（57 个例子）。该催化可以在克级进行，并已应用于药物分子的合成。
• Design, synthesis, and structure activity relationship (SAR) studies of novel imidazo[1,2-a] pyridine derivatives as Nek2 inhibitors
  作者：Haili Wang、Yunzhong Chen、Xiaofan Gu、Jianbei Xi、Ziwei Ren、Shuting Wang、Yanhong Duan、Hongyu Li、Tong Zhu、Yijie Du、Xiongwen Zhang、Mingliang Ma

  DOI：10.1016/j.bmc.2020.115775

  日期：2020.12

  cycle checkpoint regulation, cell division, DNA damage response and cell apoptosis. Nek2 has been reported to be overexpressed in various tumors and correlated with poor prognosis. Herein, a series of imidazo[1,2-a] pyridines Nek2 inhibitors were designed, synthesized, and their biological activities were investigated. Besides, structure activity relationship analysis of these compounds were performed in

  有丝分裂（NIMA）相关激酶2（Nek2）从不参与多个细胞过程，例如细胞周期检查点调节，细胞分裂，DNA损伤反应和细胞凋亡。据报道，Nek2在多种肿瘤中过表达，并与不良预后相关。在此，设计，合成了一系列咪唑并[1,2- a ]吡啶Nek2抑制剂，并对其生物学活性进行了研究。此外，在MGC-803细胞中进行了这些化合物的结构活性关系分析。筛选结果令人鼓舞，化合物28e具有良好的IC 50抑制增殖活性为38 nM。该结果将有助于设计和开发更有效的Nek2抑制剂来治疗胃癌。
• [EN] 3-(INDOLYL)- OR 3-(AZAINDOLYL)-4-ARYLMALEIMIDE COMPOUNDS AND THEIR USE IN TUMOR TREATMENT<br/>[FR] COMPOSÉS DE 3-(INDOLYL) OU 3-(AZAINDOLYL)-4-ARYLMALÉIMIDE ET LEUR UTILISATION DANS LE TRAITEMENT DES TUMEURS
  申请人：UNIV MAINZ JOHANNES GUTENBERG

  公开号：WO2011073092A1

  公开（公告）日：2011-06-23

  The present invention relates to a compound of formula (I) wherein R1, R2 and R3 are as defined in the description and the physiologically acceptable salts thereof as well as the physiologically acceptable solvates of the compounds of formula I and of the salts thereof. The compounds of formula I are suitable for treating tumors.

  本发明涉及一种化合物，其化学式为（I），其中R1、R2和R3如描述中所定义，并且其生理上可接受的盐以及化合物（I）及其盐的生理上可接受的溶剂。化合物（I）适用于治疗肿瘤。