4-溴-2,5-二甲基-1H-吡咯-3-羧酸甲酯 | 120935-94-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4-溴-2,5-二甲基-1H-吡咯-3-羧酸甲酯
• 英文名称: methyl 4-bromo-2,5-dimethyl-1H-pyrrole-3-carboxylate
• CAS: 120935-94-6
• 化学式: C₈H₁₀BrNO₂
• 分子量: 232.077
• InChiKey: LGBDYFSMZPRVLL-UHFFFAOYSA-N

物化性质

• 沸点：
  344.5±37.0 °C(Predicted)
• 密度：
  1.503±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 安全说明：
  S26,S37/39
• 储存条件：
  2-8°C

SDS

Name:	Methyl 4-bromo-2 5-dimethyl-1h-pyrrole-3-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	120935-94-6

Section 1 - Chemical Product MSDS Name:Methyl 4-bromo-2 5-dimethyl-1h-pyrrole-3-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
120935-94-6	Methyl 4-bromo-2,5-dimethyl-1H-pyrrole	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes 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. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 120935-94-6: 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: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C8H10BrNO2
Molecular Weight: 232.08

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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, halogenated agents, halogens.
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# 120935-94-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 4-bromo-2,5-dimethyl-1H-pyrrole-3-carboxylate - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 120935-94-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 120935-94-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 120935-94-6 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：

  4-溴-2,5-二甲基-1H-吡咯-3-羧酸甲酯 在 正丁基锂 、 三氟化硼乙醚 、 苄基三甲基氢氧化铵 、 sodium hydride 作用下， 反应 5.0h， 生成 2,5-二甲基-4-[2-(苯基甲基)苯甲酰]-1H-吡咯-3-羧酸甲酯
  参考文献：
  名称：

  Discovery and synthesis of methyl 2,5-dimethyl-4-[2-(phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate (FPL 64176) and analogs: the first examples of a new class of calcium channel activator

  摘要：

  Methyl 2,5-dimethyl-4-[2-(phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate, FPL 64176 (1), is the first example of a new class of calcium channel activator (CCA) that does not act on any of the well-defined calcium channel modulator receptor sites, as typified by verapamil, diltiazem, and the dihydropyridines. The potent activity of 1, having the 2-(phenylmethyl)benzoyl substituent, was predicted using QSAR on an initial set of less potent benzoylpyrroles. When compared to the CCA Bay K 8644, 1 has simialr potency on calcium uptake into GH3 cells (both have EC50 approximately 0.015 muM) but is appreciably more potent functionally at increasing contractility in a guinea pig atria preparation (1 has EC50 = 0.049 muM vs Bay K 8644 EC50 = 1.95 muM). 1 is an achiral, pharmacologically clean agonist with no demonstrable partial agonist properties and possesses appreciably higher efficacy than Bay K 8644. It should therefore become a useful biochemical and pharmacological tool for the study of calcium channels in many cell types.

  DOI：

  10.1021/jm00071a004
• 作为产物：
  描述：

  2,5-二氯吡咯-3-羧酸甲酯 在 pyridinium hydrobromide perbromide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-溴-2,5-二甲基-1H-吡咯-3-羧酸甲酯
  参考文献：
  名称：

  [EN] COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF ANDROGEN RECEPTOR AND ASSOCIATED METHODS OF USE
  [FR] COMPOSÉS ET MÉTHODES POUR LA DÉGRADATION CIBLÉE DU RÉCEPTEUR DES ANDROGÈNES ET MÉTHODES D'UTILISATION ASSOCIÉES

  摘要：

  本文描述了具有雄激素受体（AR）调节剂作用的双功能化合物。具体而言，本公开的双功能化合物在一端包含结合到 cereblon E3 泛素连接酶的一个部分，在另一端包含结合 AR 的一个部分，从而使目标蛋白质靠近泛素连接酶，以促进目标蛋白质的降解（和抑制）。本公开的双功能化合物表现出与目标蛋白质的降解/抑制相关的广泛药理活性。使用本公开的化合物和组合物治疗或预防由于目标蛋白质异常调节而导致的疾病或障碍。

  公开号：

  WO2022098544A1

文献信息

• Pyrrole derivatives, process for their preparation and pharmaceutical compositions containing them
  申请人：FISONS plc

  公开号：EP0300688A1

  公开（公告）日：1989-01-25

  Compounds of formula I, wherein R₁, R₂, R₃ and R₅ have the meanings defined in the specification, G2 represents a chain -(CH₂)z(W)y-, in which W has various meanings including C=O, and up to two of the methylene segments in the chain (CH₂)z are optionally replaced by -NH- and one segment is optionally replaced by -O- or -(C=NR₄₀)-, and the chain is optionally unsaturated and optionally substituted, and A is a 5- or 6-membered ring or a bicyclic or tricyclic fused ring system, A being optionally substituted by various substituents, possess useful pharmacological properties, in particular as cardiotonics. Also described are processes for the preparation of compounds of formula I, pharmaceutical compositions containing them and methods of treatment involving their use.

  式I的化合物，其中R₁、R₂、R₃和R₅的含义如规范中定义，G2代表一个链-(CH₂)z(W)y-，其中W具有包括C=O在内的各种含义，并且链中的(CH₂)z的最多两个亚甲基段可以选择性地被-NH-替换，一个段可以选择性地被-O-或-(C=NR₄₀)-替换，链可以是不饱和的和/或选择性地被取代的，A是一个5-或6-成员环或一个双环或三环融合环系统，A可以选择性地被各种取代基取代，具有有用的药理学性质，尤其是作为心力衰竭药。还描述了制备式I化合物的方法、含有它们的制药组合物以及涉及其使用的治疗方法。
• Androgen receptor antagonists
  申请人：Furuya Shuichi

  公开号：US20050101657A1

  公开（公告）日：2005-05-12

  The present invention provides an androgen receptor antagonistic agent and a superior prophylactic or therapeutic agent for hormone-sensitive cancer, which contain a compound of the formula: wherein, R 1 is a hydrogen atom, a group binding through a carbon atom, a group binding through a nitrogen atom, a group binding through an oxygen atom or a group binding through a sulfur atom, R 2 is a hydrogen atom, a group binding through a carbon atom, a group binding through a nitrogen atom, a group binding through an oxygen atom or a group binding through a sulfur atom, R 3 is a hydrogen atom, a hydrocarbon group which may have substituent(s), an acyl group or a heterocyclic group which may have substituent(s), R 4 is a hydrogen atom, a group binding through a carbon atom, a group binding through a nitrogen atom, a group binding through an oxygen atom or a group binding through a sulfur atom, and R 5 is a cyclic group which may have substituent(s); or a salt thereof, or its prodrug.

  本发明提供了一种雄激素受体拮抗剂，以及一种优越的预防或治疗激素敏感性癌症的药物，其含有式中的化合物：其中，R1是氢原子、通过碳原子结合的基团、通过氮原子结合的基团、通过氧原子结合的基团或通过硫原子结合的基团，R2是氢原子、通过碳原子结合的基团、通过氮原子结合的基团、通过氧原子结合的基团或通过硫原子结合的基团，R3是氢原子、可能具有取代基的碳氢基团、酰基或可能具有取代基的杂环基团，R4是氢原子、通过碳原子结合的基团、通过氮原子结合的基团、通过氧原子结合的基团或通过硫原子结合的基团，R5是可能具有取代基的环状基团；或其盐或前药。
• COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF ANDROGEN RECEPTOR AND ASSOCIATED METHODS OF USE
  申请人：Arvinas Operations, Inc.

  公开号：US20220144809A1

  公开（公告）日：2022-05-12

  Bifunctional compounds, which find utility as modulators of androgen receptor (AR), are described herein. In particular, the bifunctional compounds of the present disclosure contain on one end a moiety that binds to the cereblon E3 ubiquitin ligase and on the other end a moiety which binds AR, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The bifunctional compounds of the present disclosure exhibit a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aberrant regulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.

  本文描述了具有雄激素受体（AR）调节剂作用的双功能化合物。特别地，本公开的双功能化合物在一端含有结合到cereblon E3泛素连接酶的基团，在另一端含有结合到AR的基团，使得靶蛋白质位于泛素连接酶附近以促进靶蛋白质的降解（和抑制）。本公开的双功能化合物表现出与靶蛋白质的降解/抑制相关的广泛的药理活性。使用本公开的化合物和组合物治疗或预防由靶蛋白质异常调节引起的疾病或障碍。
• EP1466902
  申请人：——

  公开号：——

  公开（公告）日：——
• Design, synthesis, and biological evaluation of 4-phenylpyrrole derivatives as novel androgen receptor antagonists
  作者：Satoshi Yamamoto、Nobuyuki Matsunaga、Takenori Hitaka、Masami Yamada、Takahito Hara、Junichi Miyazaki、Takashi Santou、Masami Kusaka、Masuo Yamaoka、Naoyuki Kanzaki、Shuichi Furuya、Akihiro Tasaka、Kazumasa Hamamura、Mitsuhiro Ito

  DOI：10.1016/j.bmc.2011.10.067

  日期：2012.1

  A series of 4-phenylpyrrole derivatives D were designed, synthesized, and evaluated for their potential as novel orally available androgen receptor antagonists therapeutically effective against castration-resistant prostate cancers. 4-Phenylpyrrole compound 1 exhibited androgen receptor (AR) antagonistic activity against T877A and W741C mutant-type ARs as well as wild-type AR. An arylmethyl group incorporated into compound 1 contributed to enhancement of antagonistic activity. Compound 4n, 1-[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile exhibited inhibitory effects on tumor cell growth against the bicalutamide-resistant LNCaP-cxD2 cell line as well as the androgen receptor-dependent JDCaP cell line in a mouse xenograft model. These results demonstrate that this series of pyrrole compounds are novel androgen receptor antagonists with efficacy against prostate cancer cells, including castration-resistant prostate cancers such as bicalutamide-resistant prostate cancer. (C) 2011 Elsevier Ltd. All rights reserved.