1-(4,5-二氢-1H-咪唑-2-基)-3,5-二甲基-1H-吡唑氢溴酸 | 132369-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(4,5-二氢-1H-咪唑-2-基)-3,5-二甲基-1H-吡唑氢溴酸
• 英文名称: 2-(3,5-dimethylpyrazolyl)-4,5-dihydroimidazole hydrobromide
• 英文别名: 1-(4,5-dihydro-1H-imidazol-2-yl)-3,5-dimethyl-1H-pyrazole hydrobromide；1-(4,5-dihydro-1H-imidazol-2-yl)-3,5-dimethylpyrazole;hydrobromide
• CAS: 132369-02-9
• 化学式: BrH*C₈H₁₂N₄
• 分子量: 245.122
• InChiKey: HDUOMQKYHVVNSA-UHFFFAOYSA-N

物化性质

• 熔点：
  305 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2933990090

SDS

Name:	1-(4 5-Dihydro-1h-imidazol-2-yl)-3 5-dimethyl-1h-pyrazole Material Safety Data Sheet
Synonym:
CAS:	132369-02-9

Section 1 - Chemical Product MSDS Name:1-(4 5-Dihydro-1h-imidazol-2-yl)-3 5-dimethyl-1h-pyrazole Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
132369-02-9	1-(4,5-Dihydro-1H-imidazol-2-yl)-3,5-d	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
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.
Notes to Physician:
Treat symptomatically and supportively.

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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# 132369-02-9: 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: white crystalline solid
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 310 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: C8H13BrN4
Molecular Weight: 245

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen bromide, bromine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 132369-02-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(4,5-Dihydro-1H-imidazol-2-yl)-3,5-dimethyl-1H-pyrazole hydrobromide - 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
No information available.
IMO
No information available.
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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 132369-02-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 132369-02-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 132369-02-9 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：

  1-(4,5-二氢-1H-咪唑-2-基)-3,5-二甲基-1H-吡唑氢溴酸 、 2-[(S)-2,4,6-trimethylphenylsulfonylamino]-3-[5-(4-aminobutyl)isoxazolin-3-ylcarbonyl]aminopropionic acid tert-butyl ester 在 4-二甲氨基吡啶 作用下， 反应 16.0h， 生成
  参考文献：
  名称：

  Isoxazolines as Potent Antagonists of the Integrin α_vβ₃

  摘要：

  Starting with lead compound 2, we sought to increase the selectivity for alpha(v)beta(3)-mediated cell adhesion by examining the effects of structural changes in both the guanidine mimetic and the substituent alpha to the carboxylate. To prepare some of the desired aminoimidazoles, a novel reductive amination utilizing a trityl-protected aminoimidazole was developed. It was found that guanidine mimetics with a wide range of pK(a)'s were potent antagonists of alpha(v)beta(3). In general, it appeared that an acylated 2-aminoimidazole guanidine mimetic imparted excellent selectivity for alpha(v)beta(3)-mediated adhesion versus alpha(IIb)beta(3)-mediated platelet aggregation, with selectivity of approximately 3 orders of magnitude observed for compounds 3g and 3h. It was also found in this series that the alpha-substituent was required for potent activity and that 2,6-disubstituted arylsulfonamides were optimal. In addition, the selective alpha(v)beta(3) antagonist 3h was found to be a potent inhibitor of alpha(v)beta(3)-mediated cell migration.

  DOI：

  10.1021/jm9900321
• 作为产物：
  描述：

  三乙酰甲烷 、 4,5-二氰咪唑-2-肼溴化氢 在 氢溴酸 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以47%的产率得到4-acetyl-1-(2-imidazolinyl)-3,5-dimethylpyrazole (2-imidazolinyl)hydrazone dihydrobromide
  参考文献：
  名称：

  三乙酰甲烷与单取代肼和and类似物的反应。4-乙酰基-3,5-二甲基吡唑a和1,3,5-三嗪衍生物的合成

  摘要：

  三乙酰甲烷（1）与a肼在酸性介质中反应，得到4-乙酰基3,5-二甲基吡唑a衍生物2,4。然而，1与硫代氨基脲或氨基脲的相似反应主要导致3,5-二甲基吡唑（6）。1的水解趋势很强，这是最后一个转化的原因，也是由于胍导致了2-氨基-4,6-二甲基嘧啶（10）和S-甲基异硫脲提供了出乎意料的2-氨基-的事实。 4-甲基-6-甲硫基1,3,5-三嗪（11）。

  DOI：

  10.1002/jhet.5570270608

文献信息

• Parallel solid-phase synthesis of vitronectin receptor (αvβ3) inhibitors
  作者：Ariamala Gopalsamy、Hui Yang、John W Ellingboe、Kenneth L Kees、Jeanne Yoon、Richard Murrills

  DOI：10.1016/s0960-894x(00)00319-x

  日期：2000.8

  A combinatorial approach for rapid optimization of a vitronectin receptor (alphavbeta3) inhibitor lead was accomplished by solid-phase synthesis. Orthogonally bis protected 2,3-diaminopropionic acid was used to immobilize the C-terminus of the molecule. Selective deprotection and functionalization of the alpha-amino group followed by acyl resorcinol scaffold attachment and N-terminus diversification

  通过固相合成完成了用于快速优化玻连蛋白受体（alphavbeta3）抑制剂前导的组合方法。正交双保护的2，3-二氨基丙酸用于固定分子的C末端。选择性脱保护和功能化的α-氨基，然后酰基间苯二酚支架附着和N末端多样化被用来探讨结构活性关系（SAR）。
• Amidine derivatives for treating amyloidosis
  申请人：Kong Xianqi

  公开号：US20050182118A1

  公开（公告）日：2005-08-18

  The present invention relates to the use of amidine compounds in the treatment of amyloid-related diseases. In particular, the invention relates to a method of treating or preventing an amyloid-related disease in a subject comprising administering to the subject a therapeutic amount of an amidine compound. Among the compounds for use according to the invention are those according to the following Formula, such that, when administered, amyloid fibril formation, neurodegeneration, or cellular toxicity is reduced or inhibited:

  本发明涉及在治疗与淀粉样蛋白相关的疾病中使用胍类化合物。具体而言，该发明涉及一种治疗或预防受试者淀粉样蛋白相关疾病的方法，包括向受试者施用治疗剂量的胍类化合物。根据该发明用于使用的化合物包括以下公式的化合物，当施用时，淀粉样蛋白纤维形成、神经退行性或细胞毒性得到减少或抑制：
• Novel Malonamide Derivatives as .ALPHA.v.BETA.3 Antagonists. Syntheses and Evaluation of 3-(3-Indolin-1-yl-3-Oxopropanoyl)aminopropanoic Acids on Vitronectin Interaction with .ALPHA.v.BETA.3.
  作者：Shinya NAGASHIMA、Seijiro AKAMATSU、Eiji KAWAMINAMI、Souichirou KAWAZOE、Tetsuro OGAMI、Yuzo MATSUMOTO、Minoru OKADA、Ken-Ichi SUZUKI、Shin-Ichi TSUKAMOTO

  DOI：10.1248/cpb.49.1420

  日期：——

  integrin alphavbeta3 antagonists, we selected SC65811 and its guanidine analogue (1) as lead compounds. Modification of the glycine part of SC65811 led to a new series of malonamide derivatives that exhibited alphavbeta3 inhibitory activity. Among them, (R,S)-3-[3-[6-(3-benzylureido)indolin-1-yl]-3-oxopropanoylamino]-3- (pyridin-3-yl)propanoic acid (43a) showed not only potent activity with an IC50

  为了找到新的整联蛋白αvbeta3拮抗剂，我们选择了SC65811及其胍类似物（1）作为先导化合物。SC65811甘氨酸部分的修饰导致了一系列新的丙二酰胺衍生物，这些衍生物表现出alphavbeta3抑制活性。其中，（R，S）-3- [3- [6-（3-苄基脲基）吲哚-1-基] -3-氧代丙酰基氨基] -3-（吡啶-3-基）丙酸（43a）未显示相对于alphaIIbbeta3，alpha5beta1和alphavbeta5，IC50值仅为3.0 nM的有效活性，而且对alphavbeta3的选择性也很好，IC50值分别为19,000、11,000和14 nM。此外，优化43a导致最有效的alphavbeta3拮抗剂（R，S）-3-（3- [6-[（4,5-二氢-1H-咪唑-2-基）氨基]吲哚-1-基] -3-氧代丙酰基氨基）-3-（喹啉-3-基）丙酸（431），IC50值为0.42 nM。
• [EN] AMIDINE DERIVATIVES FOR TREATING AMYLOIDOSIS<br/>[FR] DERIVES D'AMIDINE POUR LE TRAITEMENT DE L'AMYLOSE
  申请人：NEUROCHEM INT LTD

  公开号：WO2005079780A1

  公开（公告）日：2005-09-01

  The present invention relates to the use of amidine compounds in the treatment of amyloid-related diseases. In particular, the invention relates to a method of treating or preventing an amyloid-related disease in a subject comprising administering to the subject a therapeutic amount of an amidine compound. Among the compounds for use according to the invention are those according to the following Formula (I), such that, when administered, amyloid fibril formation, neurodegeneration, or cellular toxicity is reduced or inhibited: Formula (I).

  本发明涉及在治疗与淀粉样蛋白相关的疾病中使用胍类化合物。具体来说，本发明涉及一种治疗或预防受试者淀粉样蛋白相关疾病的方法，包括向受试者施用治疗量的胍类化合物。根据本发明使用的化合物中包括根据以下式（I）的化合物，当施用时，可以减少或抑制淀粉样纤维形成、神经退行性或细胞毒性：式（I）。
• Discovery of Bis-Imidazoline Derivatives as New CXCR4 Ligands
  作者：Zhicheng Zhou、Isabelle Staropoli、Anne Brelot、Peggy Suzanne、Aurélien Lesnard、Fanny Fontaine、Serge Perato、Sylvain Rault、Olivier Helynck、Fernando Arenzana-Seisdedos、Jana Sopkova-de Oliveira Santos、Bernard Lagane、Hélène Munier-Lehmann、Philippe Colin

  DOI：10.3390/molecules28031156

  日期：——

  functions of CXCR4 that they influence. Site-directed mutagenesis and molecular docking predict that the alkyl chain folds in such a way that the two imidazole groups become lodged in the transmembrane binding cavity of CXCR4. Results also suggest that the alkyl chain length influences how the imidazole rings positions in the cavity. These results may provide a basis for the design of new CXCR4 antagonists

  趋化因子受体 CXCR4 及其配体 CXCL12 调节白细胞运输、稳态和功能，是许多疾病（如 HIV-1 感染和癌症）的潜在治疗靶点。在这里，我们使用基于 FRET 的高通量筛选测定法在 CERMN 化学库中鉴定了新的 CXCR4 配体。这些是包含两个通过烷基链连接的咪唑环的双咪唑啉化合物。这些分子以亚微摩尔的效力取代 CXCL12 结合，类似于 AMD3100，唯一市售的 CXCR4 配体。它们还抑制抗 CXCR4 mAb 12G5 结合、CXCL12 介导的趋化性和 HIV-1 感染。对新合成的衍生物的进一步研究指出了烷基链长度对双咪唑啉特性的影响，具有等于 8、10 或 12 的偶数个碳的分子是最有效的。有趣的是，它们在它们影响的 CXCR4 功能上有所不同。定点诱变和分子对接预测烷基链折叠的方式使得两个咪唑基团进入 CXCR4 的跨膜结合腔。结果还表明，烷基链长度会影响咪唑环在空腔