(1R,2R)-cyclopropane-1,2-dicarbonyl dichloride

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2R)-cyclopropane-1,2-dicarbonyl dichloride
• 英文别名: rel-(1R,2R)-cyclopropane-1,2-dicarbonyl dichloride；(1R,2R)-cyclopropane-1,2-dicarbonyl chloride
• 化学式: C₅H₄Cl₂O₂
• 分子量: 166.992
• InChiKey: KAERQEWUBIXISE-PWNYCUMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R)-cyclopropane-1,2-dicarbonyl dichloride 在 盐酸 、 氨 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 4.0h， 生成 N,N'-bis(4-amidinophenyl)-trans-1,2-cyclopropane dicarboxamide
  参考文献：
  名称：

  Trypanocidal Activity of Conformationally Restricted Pentamidine Congeners

  摘要：

  A series of conformationally restricted congeners of pentamidine in which the flexible pentyl bridge of pentamidine was replaced by trans-1,2-bismethylenecyclopropyl, phenyl, pyridinyl, piperazinyl, homopiperazinyl, and piperidinyl groups were synthesized. The compounds were evaluated for trypanocidal activity in vitro and in vivo against one drug-sensitive and three drug-resistant trypanosome isolates. The DNA binding affinity of the compounds was also studied using calf thymus DNA and poly(dA-dT). The nature of the linker influenced the DNA binding affinity as well as the trypanocidal activity of the compounds. trans-1,2-Bis(4-amidinophenoxymethylene)cyclopropane (1) was over 25-fold more potent than pentamidine against the drug-resistant isolate KETRI 243As-10-3, albeit with comparable DNA binding affinity. NN'-Bis(4-amidinophenyl)homopiperazine (8) was the most potent trypanocide in vitro against all four trypanosome isolates studied, but N,N'-bis(4-amidinophenyl)piperazine (6) was the most effective agent in vivo against both drug-sensitive and drug-resistant trypanosomes.

  DOI：

  10.1021/jm020375q
• 作为产物：
  描述：

  反式 环丙烷-1,2-二羧酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 (1R,2R)-cyclopropane-1,2-dicarbonyl dichloride
  参考文献：
  名称：

  Photodecarbonylation of chiral cyclobutanones

  摘要：

  三重光敏辐照2(S),3(R)-双[(苯甲酰氧基)甲基]环丁酮，在非极性分馏物中主要生成光学纯的(−)E-1(S),2(S)-双(苯甲酰氧基甲基)环丙烷，同时还有其立体异构体和环消除产物。手性环丙烷的绝对立体化学通过独立合成和合成前体的X射线晶体结构测定来确定。脱羰基化和环消除产物的分布与底物浓度呈反比关系。在四氢呋喃或苯中辐照相同的酮主要生成环消除产物。添加米克勒酮增加了光解脱羰作用的比例，表明了这一过程的三重态途径。通过添加二氰乙烯来证实这一点，显示了光解脱羰作用的显著猝灭。在丙酮中辐照2(S)-[(苯甲酰氧基)甲基]环丁烷产生相应的环丙烷作为主要产物。关键词：光解脱羰作用，手性环丙烷，环丁酮，三重敏化。

  DOI：

  10.1139/v97-060

文献信息

• [EN] ALKYLBORONIC ACIDS AS ARGINASE INHIBITORS<br/>[FR] ACIDES ALKYLBORONIQUES EN TANT QU'INHIBITEURS D'ARGINASE
  申请人：GUANGDONG NEWOPP BIOPHARMACEUTICALS CO LTD

  公开号：WO2020160707A1

  公开（公告）日：2020-08-13

  Provided are alkylboronic acids as arginase inhibitors represented by formula (I), or a pharmaceutically acceptable salt, stereoisomer, tautomer, or prodrug thereof and a pharmaceutical composition comprising said compounds.

  提供的是以化学式(I)表示的烷基硼酸作为精氨酸酶抑制剂，或其药用可接受的盐、立体异构体、互变异构体或前药，以及包含该化合物的药物组合物。
• [EN] 2-PYRIDYL CARBOXAMIDE-CONTAINING SPLEEN TYROSINE KINASE (SYK) INHIBITORS<br/>[FR] INHIBITEURS DE TYROSINE KINASE DE LA RATE (SYK) CONTENANT UN 2-PYRIDYL CARBOXAMIDE
  申请人：MERCK SHARP & DOHME

  公开号：WO2013052394A1

  公开（公告）日：2013-04-11

  The invention provides certain 2-pyridyl carboxamide-containing compounds of the Formula (I) or pharmaceutically acceptable salts thereof, wherein A and B are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions mediated by Spleen Tyrosine Kinase (Syk) kinase.

  本发明提供了一些含有2-吡啶甲酰胺的化合物，其化学式为(I)或药用可接受的盐，其中A和B按本发明定义。本发明还提供了包含这些化合物的药物组合物，以及使用这些化合物来治疗由脾酪氨酸激酶（Syk）介导的疾病或状况的方法。
• Cycloalkyl substituted polyamines for cancer therapy and methods of synthesis therefor
  申请人：SLIL Biomedical Corporation

  公开号：US20030195377A1

  公开（公告）日：2003-10-16

  Conformationally restricted polyamine compounds useful in treatment of cancer and other diseases marked by abnormal cell proliferation are disclosed. Improved methods of synthesizing such compounds are also disclosed. In one method of the invention, a carbene-bearing or carbene equivalent-bearing compound is reacted with the double bond of an alkene compound to form a cyclopropyl ring as the first step in the synthesis.

  抑制构象限制的多胺化合物可用于治疗癌症和其他以异常细胞增殖为特征的疾病。改进的合成这类化合物的方法也被揭示。在该发明的一种方法中，带有卡宾基或卡宾等效基团的化合物与烯烃化合物的双键发生反应，形成环丙基环作为合成的第一步。
• Photodecarbonylation of chiral cyclobutanones
  作者：Jailall Ramnauth、Edward Lee-Ruff

  DOI：10.1139/v97-060

  日期：1997.5.1

  Triplet photosensitized irradiation of 2(S),3(R)-bis[(benzoyloxy)methyl]cyclobutanone gave optically pure (−)E-1(S),2(S)-bis(benzoyloxymethyl)cyclopropane as a major product in the nonpolar fraction along with its stereoisomer and cycloelimination products. The absolute stereochemistry of the chiral cyclopropane was established by independent synthesis and X-ray crystal structure determination of a synthetic precursor. The distribution of decarbonylation and cycloelimination products was inversely dependent on the concentration of the substrate. Irradiation of the same ketone in tetrahydrofuran or benzene gave mostly cycloelimination products. Addition of Michler's ketone increased the ratio of photodecarbonylation, suggesting a triplet state pathway for this process. This was corroborated by the addition of dicyanoethylene, which showed significant quenching of photodecarbonylation. Irradiation of 2(S)-[(benzoyloxy)methyl]cyclobutane in acetone gave the corresponding cyclopropane as the principal product. Keywords: photodecarbonylation, chiral cyclopropanes, cyclobutanones, triplet sensitization.

  三重光敏辐照2(S),3(R)-双[(苯甲酰氧基)甲基]环丁酮，在非极性分馏物中主要生成光学纯的(−)E-1(S),2(S)-双(苯甲酰氧基甲基)环丙烷，同时还有其立体异构体和环消除产物。手性环丙烷的绝对立体化学通过独立合成和合成前体的X射线晶体结构测定来确定。脱羰基化和环消除产物的分布与底物浓度呈反比关系。在四氢呋喃或苯中辐照相同的酮主要生成环消除产物。添加米克勒酮增加了光解脱羰作用的比例，表明了这一过程的三重态途径。通过添加二氰乙烯来证实这一点，显示了光解脱羰作用的显著猝灭。在丙酮中辐照2(S)-[(苯甲酰氧基)甲基]环丁烷产生相应的环丙烷作为主要产物。关键词：光解脱羰作用，手性环丙烷，环丁酮，三重敏化。
• [EN] CYCLOALKYL SUBSTITUTED POLYAMINES FOR CANCER THERAPY AND METHODS OF SYNTHESIS THEREFOR<br/>[FR] POLYAMINES SUBSTITUEES PAR UN CYCLOALKYLE POUR LE TRAITEMENT DU CANCER, ET PROCEDES DE SYNTHESE DE CELLES-CI
  申请人：SLIL BIOMEDICAL CORP

  公开号：WO2003050072A1

  公开（公告）日：2003-06-19

  Conformationally restricted polyamine compounds useful in treatment of cancer and other diseases marked by abnormal cell proliferation are disclosed. Improved methods of synthesizing such compounds are also disclosed. In one method of the invention, a carbene-bearing or carbene equivalent-bearing compound is reacted with the double bond of an alkene compound to form a cyclopropyl ring as the first step in the synthesis.

  本发明公开了在治疗癌症和其他由异常细胞增殖标记的疾病中有用的构象限制的多胺化合物。还公开了改进的合成这种化合物的方法。在本发明的一种方法中，通过将含有卡宾或卡宾等效物的化合物与烯烃化合物的双键反应，形成环丙基环作为合成的第一步。